Potassium Cyanide → 1-Cyano-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

HRID 1439772Notes

Reaction equation

HRID 1439772 reaction equation
[C-:1]#[N:2].[K+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:22])([CH3:21])[CH2:18][CH2:19]O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1.C1(S([O-])(=O)=O)C=CC=CC=1>CN(C=O)C>[C:1]([CH2:19][CH2:18][C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[CH:10][C:5]([F:4])=[CH:6][CH:7]=2)=[CH:12][CH:13]=1)([OH:22])[CH3:21])#[N:2]

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 867352293-(4'-Fluoro-4-biphenylyl)-butane-1,3-diol 1-benzenesulfonate

Product 1

HCID 213964731-Cyano-3-(4'-fluoro-4-biphenylyl)-butan-3-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

9.7 g. of KCN are dissolved in 150 ml. of DMF and a solution of 40 g. of 3-(4'-fluoro-4-biphenylyl)-butane-1,3-diol-1-benzenesulfonate in 150 ml. of DMF is added dropwise at 20°, while stirring. The mixture is heated to 80° for 6 hours, poured onto ice water and worked up in the customary manner to give 1-cyano-3-(4'-fluoro-4-biphenylyl)-butan-3-ol, m.p. 118° - 120°.

Workup

  1. temperatureThe mixture is heated to 80° for 6 hours
  2. additionpoured onto ice water

Sources & evidence

ORD record
ord-345101ea71e6431ab094e2182780aa29
Source dataset
uspto-grants-1977_11
Patent number
US04060633

Reaction notes

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