Water → HCID 19418499, compound

HRID 864711Notes

Reaction equation

HRID 864711 reaction equation
[Si:1]([O:18][C:19]1[C:24]([CH3:25])=[C:23]([CH:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])[C:22]([OH:42])=[C:21]([CH3:43])[C:20]=1[CH3:44])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:45](Cl)(=[O:47])[CH3:46].O>ClCCl.C(N(CC)CC)C>[C:45]([O:42][C:22]1[C:23]([CH:26]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][CH3:35])=[O:33])=[C:24]([CH3:25])[C:19]([O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:20]([CH3:44])[C:21]=1[CH3:43])(=[O:47])[CH3:46]

Participants

6

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 19418518HCID 19418518, compound

Product 1

HCID 19418499HCID 19418499, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

4-tert-Butyldiphenylsilyloxy-1-hydroxy-6-(6-methoxycarbonyl-1-phenylhexyl)-2,3,5-trimethylbenzene (22.2 g, 36.46 mM) was dissolved in dichloromethane (200 ml) and triethylamine (8.3 ml, 59.9 mM). Acetyl chloride (4.1 ml, 57.7 mM) was added under ice-cooling, and the mixture was stirred for 2 hours. The reaction mixture was poured into ice-cooled water (100 ml) and stirred for 20 minutes. Then the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated to obtain 1-acetoxy-4-tert-butyldiphenylsilyloxy-6-(6-methoxycarbonyl-1-phenylhexyl)-2,3,5-trimethylbenzene as a pale yellow oil. This oil was dissolved in tetrahydrofuran (70 ml). 1M tetra-n-butylammonium fluoride trihydrate/tetrahydrofuran solution (73 ml) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice-cooled water (150 ml) and extracted with ethyl acetate (150 ml). The organic layer was washed with water followed by saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was recrystallized from hexane to obtain the desired compound as pale yellow prisms (9.03 g).

Workup

  1. temperaturecooling
  2. additionThe reaction mixture was poured into ice-
  3. stirringstirred for 20 minutes
  4. washThen the organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f33100310274ef1990d194017ebef65
Source dataset
uspto-grants-1996_10
Patent number
US05563129

Reaction notes

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