Ethyl 2-formylcyclopropanecarboxylate → Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

HRID 561879

Reaction equation

HRID 561879 reaction equation
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 2

HCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 4311764Sodium borohydride

Product 1

HCID 13005707Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 2-formylcyclopropanecarboxylate in methanol (0.7 M) was added at −0° C. sodium borohydride portionwise. The resulting reaction mixture was stirred at 0° C. for 30 min and then at RT for 1.5 h. The reaction was quenched with sat. aq. NH4Cl and then extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, and filtered. Concentrated of the filtrate in vacuo afforded the title compound as a colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. waitat RT for 1.5 h
  3. customThe reaction was quenched with sat. aq. NH4Cl
  4. extractionextracted with ether
  5. washThe combined organic extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationConcentrated of the filtrate in vacuo

Sources & evidence

ORD record
ord-f34373fe7b3049a9afa4148cfd5a6077
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Linked notes

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