Carbon Tetrachloride → Z-1-[4-(2-benzyloxyethoxy)-phenyl]-1-(4-benzyloxyphenyl)-4-chloro-2-phenylbut-1-ene

HRID 1289921Notes

Reaction equation

HRID 1289921 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)=[C:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:20][CH2:21]O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:63]>C(#N)C>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15](/[C:18](/[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:31][CH:30]=2)=[C:19](\[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)/[CH2:20][CH2:21][Cl:63])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 539001484-[4-(2-Benzyloxyethoxy)-phenyl]-4-(4-benzyloxyphenyl)-3-phenylbut-3-en-1-ol

Product 1

HCID 67564316Z-1-[4-(2-benzyloxyethoxy)-phenyl]-1-(4-benzyloxyphenyl)-4-chloro-2-phenylbut-1-ene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-[4-(2-benzyloxyethoxy)-phenyl]-4-(4-benzyloxyphenyl)-3-phenylbut-3-en-1-ol (1.9 g, 3.45 mmol), triphenyl phosphine (1.8 g, 6.9 mmol), carbon tetrachloride (2.6 g, 17.25 mmol) and acetonitrile (10 ml) were stirred at room temperature for an hour. The product was separated by the same method as Z-1-[4-(2-benzyloxyethoxy)-phenyl]-4-chloro-1,2-diphenyl-but-1-ene described in example 2 and purified by flash chromatography (toluene: methanol, 9.75:0.25). Yield 1.2 g.

Workup

  1. customThe product was separated by the same method as Z-1-[4-(2-benzyloxyethoxy)-phenyl]-4-chloro-1,2-diphenyl-but-1-ene
  2. custompurified by flash chromatography (toluene: methanol, 9.75:0.25)

Sources & evidence

ORD record
ord-2ee39505555d44dd88159ded62c56803
Source dataset
uspto-grants-1998_05
Patent number
US05750576

Reaction notes

Loading…