Water → 2-(1-cyclopropylethoxy)Acetic acid

HRID 376353

반응식

HRID 376353 반응식
[H-].[Na+].Br[CH2:4][C:5]([OH:7])=[O:6].[CH3:8][CH:9]([CH:11]1[CH2:13][CH2:12]1)[OH:10].O>C1COCC1>[CH:11]1([CH:9]([O:10][CH2:4][C:5]([OH:7])=[O:6])[CH3:8])[CH2:13][CH2:12]1

참가 물질

6

반응물 4

HCID 962WaterHCID 6227Bromoacetic AcidHCID 24758Sodium hydrideHCID 791041-Cyclopropylethanol

생성물 1

HCID 221142352-(1-cyclopropylethoxy)Acetic acid수율 29.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a suspension of NaH (80% in oil) (15.7 g, 523 inmol) in THF (180 mL) at 0° C. were added bromoacetic acid (28.0 g, 203 mmol) and a-methylcyclopropane methanol (10.0 g, 116 mmol). The resulting mixture was then stirred at 70° C. After a period of 18 h, the reaction mixture was poured over cold H2O and the H2O phase was extracted once with Et2O. The water phase was acidified with HCl and extracted twice with Et2O. The ether was dried over MgSO4, filtered and evaporated under reduced pressure. The crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH) to provide 5.0 g of the title compound.

후처리

  1. extractionthe H2O phase was extracted once with Et2O
  2. extractionextracted twice with Et2O
  3. dry with materialThe ether was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude oil was then purified by flash chromotography (40% EtOAc in hexane to 40% EtOAc in Hexane+AcOH)

출처 및 근거

ORD 기록
ord-ea01a07f1b7b437c8165fa26e3c444d7
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06020343

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