Dimethylformamide → Benzyl trans-2-(2-(hydroxymethyl)cyclopropyl)acetate

HRID 2202264Notes

Reaction equation

HRID 2202264 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:5][C@H:4]1[CH2:6][C:7]([OH:9])=[O:8].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[OH:1][CH2:2][C@@H:3]1[CH2:5][C@H:4]1[CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 118622767trans-2-(2-(Hydroxymethyl)cyclopropyl)acetic acid

Product 1

HCID 118622745Benzyl trans-2-(2-(hydroxymethyl)cyclopropyl)acetateYield 52.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of trans-2-(2-(hydroxymethyl)cyclopropyl)acetic acid (50 mg, 0.38 mmol), benzyl bromide (0.050 mL, 0.42 mmol), potassium carbonate (58.4 mg, 0.42 mmol) and DMF (2 mL) was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→80% ethyl acetate/hexane) to give benzyl trans-2-(2-(hydroxymethyl)cyclopropyl)acetate (44.0 mg, 0.200 mmol, 52%) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→80% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dcc3624595804805a78bc47c519bff7f
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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