Water → HCID 22408176, compound

HRID 439802Notes

Reaction equation

HRID 439802 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:24]=[CH:23][C:13]([CH:14]([OH:22])[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[C:12]([CH3:25])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:26](Cl)(=[O:28])[CH3:27].C(Cl)Cl.[OH2:33]>N1C=CC=CC=1.CN(C1C=CC=CN=1)C>[C:26]([O:22][C:14]([OH:33])([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1)[C:13]1[CH:23]=[CH:24][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])=[CH:11][C:12]=1[CH3:25])(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 22408140HCID 22408140, compound

Product 1

HCID 22408176HCID 22408176, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 1049PyridineSolvent

Procedure

4-t-Butyldimethylsilyloxymethyl-2,3'-dimethylbenzhydrol (6 g, 16.8 millimol) was dissolved in pyridine (10 ml), and thereto was added dimethylaminopyridine (200 mg, 1,6 millimol), and the mixture was cooled with ice. To the mixture were added acetylchloride (1.54 g, 19.6 millimol) and methylene chloride (10 ml). The mixture was returned to room temperature, and stirred for 2 hours. After adding water, the mixture was extracted with ethyl acetate, the organic layer was washed with in turn dil. hydrochloric acid, water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate. The solvent was distilled away to give the title compound (6.9 g, 16.6 millimol, 99%).

Workup

  1. temperaturethe mixture was cooled with ice
  2. customwas returned to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with in turn dil. hydrochloric acid, water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled away

Sources & evidence

ORD record
ord-ee12f33b4cb24822a54f596a489540e3
Source dataset
uspto-grants-1996_05
Patent number
US05516777

Reaction notes

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