Diethyl Ether → 2-Chloro-alpha-cyclopropyl-4-methylbenZenemethanol
Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[C:11]([CH:13]1[CH2:15][CH2:14]1)=[O:12].[Cl-].[NH4+].C(OCC)C>C(O)C.C(OCC)(=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[CH:11]([CH:13]1[CH2:15][CH2:14]1)[OH:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
51.3 mg (1.36 mmol) of sodium borohydride were added to 320 mg (1.23 mmol) of the compound from Example 125A in 5 ml of ethanol and 1 ml of ethyl acetate under argon, and the mixture was stirred at 40° C. for 2 h. Then a further 46.6 mg (1.23 mmol) of sodium borohydride were added, and the mixture was stirred at 40° C. overnight. The reaction mixture was added to saturated aqueous ammonium chloride solution and diethyl ether, the phases were separated, the aqueous phase was extracted twice with diethyl ether, and the combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. 307 mg of the title compound were obtained and were reacted without further purification.
Workup
- stirringthe mixture was stirred at 40° C. overnight
- customthe phases were separated
- extractionthe aqueous phase was extracted twice with diethyl ether
- washthe combined organic phases were washed with saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f0acd68b546c4d2e8aa9d674f233bcf2
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063234B2
Reaction notes
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