Dimethyl Sulfoxide → p-(6-Methoxy-2-phenyl-3,4-dihydro-1-naphthyl)phenol
Reaction equation
CC(C)([O-])C.[K+].CS(C)=O.[Cl-].[NH4+].I[CH:14]1[CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]([C:30]2[CH:35]=[CH:34][C:33]([O:36]C(=O)C(C)(C)C)=[CH:32][CH:31]=2)[C:21]2[C:16](=[CH:17][C:18]([O:43][CH3:44])=[CH:19][CH:20]=2)[CH2:15]1>>[OH:36][C:33]1[CH:32]=[CH:31][C:30]([C:22]2[C:21]3[C:16](=[CH:17][C:18]([O:43][CH3:44])=[CH:19][CH:20]=3)[CH2:15][CH2:14][C:23]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:35][CH:34]=1Participants
Conditions
- Temperature
- 90 °C
Procedure
Potassium tert-butoxide solution 0.5 mol/L in dimethyl sulfoxide (1.10 mL, 0.55 mmol) was added to and dissolved in 2-iodo-7-methoxy-3-phenyl-4-(4-pivaloyloxyphenyl)-1,2,3,4-tetrahydronaphthalene (5′, 74.4 mg, 0.138 mmol) under an argon atmosphere, and the resulting aubergine solution was stirred for 1 hour while heating at 90° C. Thereafter, the reaction mixture was cooled with ice, and then a saturated aqueous ammonium chloride solution (7 mL) was added thereto and sufficiently stirred, followed by extracting four times with a mixed liquid (4 mL) of hexane/diethyl ether (1:1). An organic layer was collected, followed by drying with anhydrous magnesium sulfate and concentration thereof. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the title compound (7, 41.1 mg, yield 89%), the same as that of Example 4.
Workup
- temperatureThereafter, the reaction mixture was cooled with ice
- stirringsufficiently stirred
- extractionby extracting four times with a mixed liquid (4 mL) of hexane/diethyl ether (1:1)
- customAn organic layer was collected
- dry with materialby drying with anhydrous magnesium sulfate and concentration
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
Sources & evidence
- ORD record
- ord-19e120eb913043daac4897823a87ca2f
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193394B2
Reaction notes
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