Water → HCID 11198381, compound

HRID 278949Notes

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

In 460 ml of dimethylformamide, 46.0 g (0.21 mole) of the 3-(3,4-dichlorophenyl)-3-oxo-1-propanol obtained in Referential Example 4(a) were dissolved, followed by the addition of 35 ml (0.25 mole) of triethylamine and 38.0 g (0.25 mole) of tert-butyldimethylchlorosilane under ice-cooling. The resulting mixture was stirred at 0° C. for 2 hours. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give a residue, which was purified by chromatography on a silica gel column (eluting solvent: n-hexane: ethyl acetate=96:4), whereby 66.1 g of the title compound were obtained as white crystals.

Workup

dissolutionwere dissolved
temperaturecooling
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure
customto give a residue, which
customwas purified by chromatography on a silica gel column (eluting solvent: n-hexane: ethyl acetate=96:4)

Sources & evidence

ORD record: ord-79c8c616357d4ea184c1736b76964adb
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362179B1

Reaction notes

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