Carbon Tetrachloride → HCID 13854291, compound

HRID 1194040Notes

Reaction equation

HRID 1194040 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1)[CH:3]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42](Cl)(Cl)([Cl:44])[Cl:43]>ClCCl.[Zn]>[CH3:1][C:2]([CH3:22])([CH:3]=[C:42]([Cl:44])[Cl:43])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 13854284HCID 13854284, compound

Product 1

HCID 13854291HCID 13854291, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,2-dimethyl-3-(3-benzyl-4-fluoro-benzyloxy)propan-1-al (0.4 g), triphenylphosphine (0.77 g), zinc dust (0.10 g) and carbon tetrachloride (3 cm3) in dichloromethane (3 ml) was heated at the reflux temperature for five hours. After cooling to the ambient temperature (ca 25° C.), the mixture was allowed to stand for 14 hours where upon it was triturated with diethylether. The solvent was evaporated under reduced pressure and the residue was passed through a short plug of silica gel using petroleum ether (boiling range 40°-60° C.) containing diethyl ether (10% by volume) as eluent to give 2,2-dimethyl-1-(3-benzyl-4-fluorobenzyloxy)-4,4-dichlorobut-3-ene (0.44 g).

Workup

  1. temperaturewas heated at the reflux temperature for five hours
  2. customwhere upon it was triturated with diethylether
  3. customThe solvent was evaporated under reduced pressure
  4. additioncontaining diethyl ether (10% by volume) as eluent

Sources & evidence

ORD record
ord-ea0b2e03841948d49cdfdc175e43d205
Source dataset
uspto-grants-1989_03
Patent number
US04812483

Reaction notes

Loading…