Tetrahydrofuran → 1-(3-Benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([Mg]Br)[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([O:25][C:26]1[CH:27]=[C:28](Br)[CH:29]=[C:30](F)C=1)C1C=CC=CC=1.[Mg].[O:35]1CCCC1>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:30]2([OH:35])[CH2:29][CH2:28][CH2:27][CH:26]2[O:25][CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Procedure
After repetition of the above reaction, a solution of 2-methocyclopentanone(12.5 g) in tetrahydrofuran (10 ml) was added to a solution of 3-benzyloxy-5-fluorophenylmagnesium bromide [prepared by heating a mixtureof 3-benzyloxy-5-fluorobromobenzene (31 g), magnesium powder (2.65 g) and tetrahydrofuran (20 ml) to 40° C. for 2 hours] and the mixture was stirred at ambient temperature for 2 hours. The mixture yes evaporated andthe residue was partitioned between diethyl ether and water. The organic layer was washed with water, dried (MgSO4) and evaporated. The residue as purified by column chromatography using a 9:1 v/v mixture of methylene chloride and diethyl ether as eluent. There was thus obtained, as a mixture of diastereoisomers, 1-(3-benzyloxy-5-fluorophenyl)-2-methoxycyclopentanol (21.7 g, 62%), as anoil.
Workup
- customAfter repetition of the above reaction
- customprepared
- customThe mixture yes evaporated andthe residue
- customwas partitioned between diethyl ether and water
- washThe organic layer was washed with water
- dry with materialdried (MgSO4)
- customevaporated
- customThe residue as purified by column chromatography
- additiona 9:1 v/v mixture of methylene chloride and diethyl ether as eluent
Sources & evidence
- ORD record
- ord-4eeaa4964e104129ada61c11fecdcf96
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05446043
Reaction notes
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