Reaction equation
[OH:1][C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[C:5]([CH3:14])([CH3:13])[CH2:4][CH2:3]1.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)Cl.CCOC(C)=O>[C:21]([O:1][C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[C:5]([CH3:13])([CH3:14])[CH2:4][CH2:3]1)(=[O:23])[CH3:22]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (+/−) ethyl 2-(1-hydroxy-1,2,3,4-tetrahydro-4,4-dimethyl-7-bromo-naphthalen-1-yl)acetate (Compound E47, 200.0 mg, 0.586 mmol) and 4-N,N-dimethylaminopyridine (86.0 mg, 0.703 mmol) in 4.0 mL CH2Cl2 at 0° C. was added acetic anhydride (239.3 mg, 2.344 mmol). The resulting solution was warmed to room temperature and stirred overnight. The reaction was warmed to 50° C. for 3 h, cooled to room temperature, and diluted with EtOAc (70 mL). The solution was washed with H2O, saturated aqueous NaHCO3, 10% aqueous HCl, and saturated aqueous NaCl, before being dried over MgSO4. Removal of the solvents under reduced pressure followed by column chromatography afforded the title compound as a colorless oil.
Workup
- temperatureThe reaction was warmed to 50° C. for 3 h
- temperaturecooled to room temperature
- washThe solution was washed with H2O, saturated aqueous NaHCO3, 10% aqueous HCl, and saturated aqueous NaCl
- dry with materialbefore being dried over MgSO4
- customRemoval of the solvents under reduced pressure
Sources & evidence
- ORD record
- ord-aa57417f51c0495fbefef82b59c95ba4
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06855832B2
Linked notes
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