Carbon Tetrachloride → HCID 18650842, compound

HRID 1609415Notes

Reaction equation

HRID 1609415 reaction equation
O[C@@H:2]([CH3:21])[CH2:3][C@@H:4]([CH3:20])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:42]>>[Cl:42][C@@H:2]([CH3:21])[CH2:3][C@H:4]([CH3:20])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57000686HCID 57000686, compound

Product 1

HCID 18650842HCID 18650842, compound

Procedure

1.8 g of the (R,S)-4-[4'-(3"-hydroxy-1"-methylbutoxy)phenyl]benzonitrile obtained in the above Example 1 was dissolved in 36 ml of carbon tetrachloride. 3.0 g of triphenylphosphine was added thereto and the obtained mixture was stirred under reflux for five hours. After distilling off the solvent, the residue was extracted with n-hexane and desolvated. The obtained residue was purified by silica gel column chromatography with the use of a mixture of n-hexane and diethyl ether (9:1) as a developing solvent. Thus, 1.50 g of (S ,S) -4-[4'-(3"-chloro-1"-methylbutoxy)phenyl]benzonitrile was obtained.

Workup

  1. temperatureunder reflux for five hours
  2. distillationAfter distilling off the solvent
  3. extractionthe residue was extracted with n-hexane
  4. customThe obtained residue was purified by silica gel column chromatography with the use of a mixture of n-hexane and diethyl ether (9:1) as a developing solvent

Sources & evidence

ORD record
ord-240ca7af105f4bceb5a0d821f1f69436
Source dataset
uspto-grants-1995_03
Patent number
US05401436

Reaction notes

Loading…