Dimethylformamide → benzyl 2-((1R,2S)-2-(hydroxymethyl)cyclopropyl)acetate
Reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][CH2:10][C@H:11]1[CH2:13][C@@H:12]1[CH2:14][C:15]([OH:17])=[O:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[OH:9][CH2:10][C@H:11]1[CH2:13][C@@H:12]1[CH2:14][C:15]([O:17][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:16]Participants
6
Procedure
Benzyl bromide (539 μL, 4.53 mmol) was added to a mixture of 2-((1R,2S)-2-(hydroxymethyl)cyclopropyl)acetic acid (536 mg, 4.12 mmol), potassium carbonate (626 mg, 4.53 mmol) and DMF (8 mL) at room temperature, and the mixture was stirred at room temperature for 15 hr. The reaction mixture was poured into water (80 mL), and the mixture was extracted with ethyl acetate (×3). The organic layer was washed with water and brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 33→53% ethyl acetate/hexane) to give benzyl 2-((1R,2S)-2-(hydroxymethyl)cyclopropyl)acetate (718 mg, 3.26 mmol, 79%) as a colorless oil.
Workup
- extractionthe mixture was extracted with ethyl acetate (×3)
- washThe organic layer was washed with water and brine
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 33→53% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-f0997b44e2f44126aa2bafd86d26191e
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365520B2
Reaction notes
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