Carbon Tetrachloride → HCID 86597206, compound

HRID 2108939Notes

Reaction equation

HRID 2108939 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 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-c0b4203a7d06425298bf13129b736011
Source dataset
uspto-grants-2009_04
Patent number
US07514461B2

Reaction notes

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