Water → HCID 11198381, compound

HRID 1275154Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:9](=[O:13])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22].O>CN(C)C=O>[Si:25]([O:12][CH2:11][CH2:10][C:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:13])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

46.0 g (0.21 mole) of 3-(3,4-dichlorophenyl)-3-oxo-1-propanol [prepared as described in step (a) above] were dissolved in 460 ml of dimethylformamide, and 35 ml (0.25 mole) of triethylamine and 38.0 g (0.25 mole) of t-butyldimethylchlorosilane were added to the resulting solution. The mixture was then stirred for 2 hours at 0° C. At the end of this time, the reaction mixture was poured into water and extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a 96:4 by volume mixture of hexane and ethyl acetate as the eluent, to give 66.1 g of the title compound as white crystals.

Workup

extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed by distillation under reduced pressure
customthe resulting residue was purified by silica gel column chromatography
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-292cc8b1902c43618deef7639d47768b
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159967

Reaction notes

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