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Water → HCID 11198381, compound

HRID 1279337
Notes
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Reaction equation

HRID 1279337 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 184275003-(3,4-Dichlorophenyl)-3-oxo-1-propanol

Product 1

HCID 11198381HCID 11198381, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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-butyldimethyl-chlorosilane 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

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

Sources & evidence

ORD record
ord-265cba4131af470a81efd808760f687c
Source dataset
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06448247B1

Reaction notes

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