Boron trifluoride etherate → HCID 86614886, compound
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][C:11]([O:16][CH2:17][CH2:18][CH:19]1[CH2:21][CH2:20]1)=[CH:10][CH:9]=3.C[Li].C([Li])CCC.[CH3:29][C:30]1([O:33][CH2:32]1)[CH3:31].B(F)(F)F.CCOCC>C1COCC1>[CH:19]1([CH2:18][CH2:17][O:16][C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[CH:7]=[CH:6][C:5]2[CH:4]=[CH:3][C:2]([CH2:29][C:30]([CH3:32])([OH:33])[CH3:31])=[CH:15][C:14]3=2)[CH2:21][CH2:20]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 3-bromo-6-(2-cyclopropylethoxy)phenanthrene (11 mmol) from Step 1 above in THF (75 mL) at −78° C. was successively added methyllithium (1.6 M in diethyl ether, 1 mL) and butyllithium (2.5 M in hexanes, 5.3 μL). The mixture was stirred at −78° C. for 30 minutes, after which isobutylene oxide (2.9 mL, 33 mmol) was added, followed by BF3.OEt2 (4.2 mL, 33 mmol). The reaction mixture was stirred at −78° C. for 1 h, then quenched with 1 M HCl. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The material was purified by flash chromatography on silica (10% ethyl acetate in hexanes) to afford 1-[6-(2-cyclopropylethoxy)-3-phenanthryl]-2-methylpropan-2-ol (1.33 g) as a yellow oil.
Workup
- customat −78° C.
- stirringThe reaction mixture was stirred at −78° C. for 1 h
- customquenched with 1 M HCl
- extractionThe aqueous layer was extracted with ethyl acetate
- washThe combined organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe material was purified by flash chromatography on silica (10% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-a3e60996352944dd8b0c6554ee584f79
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943649B2
Reaction notes
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