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17th July 2017 @ 20:12

Scheme:

Screen Shot 2017-07-17 at 2.58.36 PM.png

Compound

MW(m)

Mol(Mmol)

Mol(M)

Mass

Density

Volume(mL)

Equiv

LDA, 2.0 M in THF

 

20.78

2

 

 

10.4

1.05

4-chlorobenzeneacetonitrile

in 30mL dry THF

151.59

19.79

 

3000 mg

 

 

1

Acetyl chloride

in 5mL dry THF

77.99

19.79

 

 

 

 

1

2-(4-chlorophenyl)-3-oxopentanenitrile

 

193.63

19.79

 

3.83 g

1.104

1.41mL

1

5/26/17 – A dry 1-neck 250 mL 24/40 round bottom flask with septum was put under Argon while 10.4 mL 2.0 M LDA in 20 mL dry THF was added to give a light-med brown-orange solution, which was cooled to ~ -80 ˚C with dry ice/acetone.  A clear, colorless solution of 4-chlorobenzeneacetonitrile in 30 mL dry THF was then added to the solution at about 4 drops/sec down the cooled side of the 250 mL RB flask to give a clear light-med brown-orange solution, which was stirred for approximately 10 minutes at ~ -80 ˚C.  With dry ice/acetone bath still in place, a clear, colorless solution of propionyl chloride in 5 mL dry THF was added dropwise at about ~ 2 drops/second to give a cloudy light-medium tan suspension, which was allowed to stir overnight and warm to room temperature slowly as the cooling bath warmed.

5/30/17 -  In the morning a light-medium tan suspension was present.  The reaction was quenched at RT with saturated aqueous ammonium chloride which afforded a clear, light-medium red-orange solution with a white/colorless solid in the bottom.

5/30/17.  The reaction mixture was transferred to a separatory funnel, and the organic layer was washed with H2O (the NH4Cl solid dissolved with addition of H2O), brine. The aqueous layer was extracted 2 x EtOAc, and the combined organic layers were dried over MgSO4 and concentrated to a dark red-brown liquid. TLC taken.

AcetylS1.png

5/31/17 -   To the resulting crude product was added a minimal amount of CH2Cl2, followed by a minimal amount of dry silica.  The volatiles were removed. The resulting silica was dry transferred onto a silica column. The product was purified with a column with the starting eluent 50:50 EtOAc/Hexanes until the last product began to come off column, followed by EtOAc to completely remove it.

6/1/17 - Fractions 45-60 and Erlenmeyer’s 1-4 were collected and concentrated on high vacuum. NMR was obtained. 

AcetylNMRCDCl3.png
Attached Files
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AcetylNMRCDCl3.png
AcetylS1.png