Carbon Tetrachloride → HCID 17968135, compound

HRID 1373995Notes

Reaction equation

HRID 1373995 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[Si:25]([O:32][C:33]1[C:41]2[O:40][C:39](CO)=[CH:38][C:37]=2[CH:36]=[CH:35][CH:34]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>C(Cl)Cl>[C:28]([Si:25]([CH3:27])([CH3:26])[O:32][C:33]1[C:41]2[O:40][C:39]([CH2:20][Cl:24])=[CH:38][C:37]=2[CH:36]=[CH:35][CH:34]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 17968143HCID 17968143, compound

Product 1

HCID 17968135HCID 17968135, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.5 g (9.5 mmol) of triphenylphosphine and 0.92 ml (9.5 mmol) of carbon tetrachloride are added to a solution of [7-(tert-butyldimethylsilanyloxy)-benzofuran-2-yl]methanol (14) (1.78 g, 6.4 mmol) in methylene chloride (9 ml), kept at 0° C. The reaction mixture is stirred at 0° C. for 1 hour and then the solvent is evaporated under reduced pressure. The residue is taken up in 30 ml of cyclohexane and stirred for 1 hour. The precipitate formed is filtered and the filtrate concentrated. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 95/5). The title product is obtained in the form of a pale yellow liquid (1.5 g).

Workup

  1. customkept at 0° C
  2. customthe solvent is evaporated under reduced pressure
  3. stirringstirred for 1 hour
  4. customThe precipitate formed
  5. filtrationis filtered
  6. concentrationthe filtrate concentrated
  7. customThe residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 95/5)

Sources & evidence

ORD record
ord-53c0c63818bb4fb4a769859543086554
Source dataset
uspto-grants-2007_01
Patent number
US07163957B2

Reaction notes

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