Water → trans-(2-((Tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol
Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Si:7]([O:24][CH2:25][C@@H:26]1[CH2:28][C@H:27]1[C:29](OCC)=[O:30])([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[Si:7]([O:24][CH2:25][C@@H:26]1[CH2:28][C@H:27]1[CH2:29][OH:30])([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of LAH (0.92 g, 24.24 mmol) in THF (100 mL) was added a solution of ethyl trans-2-((tert-butyldiphenylsilyloxy)methyl)cyclopropanecarboxylate (21.4 g, 55.94 mmol) in THF (20 mL) at 0° C., and the mixture was stirred for 2 hr. To the reaction mixture were added successively water (0.92 mL), 15% aqueous sodium hydroxide solution (0.92 mL) and water (2.76 mL). The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 1→30% ethyl acetate/hexane) to give trans-(2-((tert-butyldiphenylsilyloxy)methyl)cyclopropyl)methanol (14.16 g, 41.66 mmol, 74%) as a colorless oil.
Workup
- customThe precipitate was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 1→30% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-d38ecb33ba0041ccb3fe1e8bc83a0809
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365520B2
Reaction notes
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