Sodium Cyanide → (3R)-3-(4-chlorophenyl)-3-cyclopropylpropanenitrile

HRID 1835032Notes

Reaction equation

CC1C=CC(S(O[CH2:12][C@@H:13]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH:14]2[CH2:16][CH2:15]2)(=O)=O)=CC=1.[C-:24]#[N:25].[Na+]>CS(C)=O>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C@@H:13]([CH:14]2[CH2:15][CH2:16]2)[CH2:12][C:24]#[N:25])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (2R)-2-(4-chlorophenyl)-2-cyclopropylethyl 4-methylbenzenesulfonate (11.00 g, 31.3 mmol) and NaCN (4.62 g, 94.3 mmol) in dimethyl sulfoxide (100 ml) is heated at to 90° C. for 3 hours. The dimethyl sulfoxide was removed in vacuo and the resulting mixture is partitioned between water (200 ml) and diethyl ether (200 ml). The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo. The residue chromatographed on silica gel eluting with ether:hexane (25:75) to afford the title compound as a colorless oil (5.62 g, 87%) which is characterized by 1HNMR, IR and mass spectral analyses.

Workup

customThe dimethyl sulfoxide was removed in vacuo
customthe resulting mixture is partitioned between water (200 ml) and diethyl ether (200 ml)
dry with materialThe organic layer is dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue chromatographed on silica gel eluting with ether:hexane (25:75)

Sources & evidence

ORD record: ord-4522356c382f41c8b938e692016c57f0
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770463B2

Reaction notes

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