Acetic Acid → HCID 58897785, compound
Reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2(OC)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Li]CCCC.C([O:27]B(OC(C)C)OC(C)C)(C)C.C(O)(=O)C.OO>C1COCC1.O>[C:11]1([C:6]2[C:7]3[C:3](=[C:2]([OH:27])[CH:10]=[CH:9][CH:8]=3)[CH2:4][CH:5]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
Under an argon atmosphere, to a solution of 21.0 g (69.3 mmol) of 4-bromo-1-methoxy-1-phenylindane in 200 ml of THF, 27.7 ml of 2.5 M nBuLi (69.3 mmol) in hexanes was added with vigorous stirring for 1 hour at −78° C. Then, 24.0 ml (19.5 g, 104 mmol) of triisopropylborate was added at this temperature. The resulting mixture was slowly warmed to ambient temperature, and then 5.96 ml (6.25 g, 104 mmol) of glacial acetic acid was added. The resulting mixture was cooled to 0° C., and then 14.7 ml of 16% H2O2 was added. This mixture was stirred for ca. 30 min at room temperature, and then 300 ml of water was added. The product was extracted with 3×150 ml of CH2Cl2. The combined extract was dried over Na2SO4 and evaporated to dryness. The analytically pure product, 3-phenyl-1H-inden-7-ol, was obtained by flash chromatography on Silica Gel 60 (40-63 μm, d 50 mm, l 350 mm, eluant: hexanes-CH2Cl2=4:1). Yield, 9.68 g (67%).
Workup
- temperatureThe resulting mixture was slowly warmed to ambient temperature
- temperatureThe resulting mixture was cooled to 0° C.
- stirringThis mixture was stirred for ca. 30 min at room temperature
- extractionThe product was extracted with 3×150 ml of CH2Cl2
- extractionThe combined extract
- dry with materialwas dried over Na2SO4
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-6e8de3d7f0164259b571d3c1e441952e
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763562B2
Reaction notes
Loading…