Carbon Tetrachloride → HCID 86597206, compound

HRID 1666750Notes

Reaction equation

HRID 1666750 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)[Cl:21].[CH3:25][O:26][CH2:27][O:28][C:29]1[C:30]([CH3:44])=[C:31]2[C:36](=[C:37]([CH3:40])[C:38]=1[CH3:39])[O:35][C:34]([CH3:43])([CH:41]=O)[CH2:33][CH2:32]2>C(Cl)Cl.[Zn]>[Cl:21][C:20]([Cl:24])=[CH:41][C:34]1([CH3:43])[CH2:33][CH2:32][C:31]2[C:36](=[C:37]([CH3:40])[C:38]([CH3:39])=[C:29]([O:28][CH2:27][O:26][CH3:25])[C:30]=2[CH3:44])[O:35]1

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 86597207HCID 86597207, compound

Product 1

HCID 86597206HCID 86597206, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine (524 mg, 2.0 mmol), carbon tetrachloride (193 ul, 2.0 mmol), Zinc dust (130 mg, 2.0 mmol) and 6-methoxymethoxy-2,5,7,8-tetramethyl-chroman-2-carbaldehyde (0.25 gram, 0.95 mmol) in 4 ml of DCM was stirred overnight at room temperature. The mixture was rinsed with hexane times and the combined solutions were dried over MgSO4. The solution was concentrated and the residue was purified via flash column chromatography on silica gel (10% ethyl acetate in hexane) to afford 320 mg of 2-(2,2-dichloro-vinyl)-6-methoxymethoxy-2,5,7,8-tetramethyl-chroman.

Workup

  1. washThe mixture was rinsed with hexane times
  2. dry with materialthe combined solutions were dried over MgSO4
  3. concentrationThe solution was concentrated
  4. customthe residue was purified via flash column chromatography on silica gel (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-271372c9ed6e482aa991b67f4d0408ff
Source dataset
uspto-grants-2011_10
Patent number
US08044097B2

Reaction notes

Loading…