Water → Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

HRID 340774

반응식

HRID 340774 반응식
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[BH4-].[Na+].O.CCOC(C)=O>CO>[CH2:9]([O:8][C:6]([CH:4]1[CH2:5][CH:3]1[CH2:1][OH:2])=[O:7])[CH3:10]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 4311764Sodium borohydride

생성물 1

HCID 13005707Ethyl 2-(hydroxymethyl)cyclopropanecarboxylate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Ethyl 2-formyl-1-cyclopropanecarboxylate (2 ml, 15.11 mmol) was dissolved in methanol (35 ml) and cooled to 0° C. under N2. Sodium borohydride (1.2 g, 31.7 mmol) was added in portions and resulting solution stirred at 0° C. for 2 h. The solution was then diluted by the dropwise addition of water, followed by the addition of EtOAc (100 mL). The aqueous layer was separated and extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine, dried over sodium sulphate and concentrated in vacuo to give the title compound. TLC: 20% EtOAc/hexanes, high Rf: 0.35, low Rf: 0.3.

후처리

  1. customresulting solution
  2. customThe aqueous layer was separated
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b04b0085714747b3a4f223f0a0842e48
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895596B2

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