Dimethylformamide → ethyl (2E)-3-(oxolan-3-yl)prop-2-enoate

HRID 41010

반응식

HRID 41010 반응식
[H-].[Na+].[CH2:3]1[CH2:7][O:6][CH2:5][CH2:4]1.[O:8]1[CH2:12][CH2:11][CH:10]([CH:13]=O)[CH2:9]1.CN(C=[O:19])C>O>[O:6]1[CH2:7][CH2:3][CH:4](/[CH:13]=[CH:10]/[C:9]([O:8][CH2:12][CH3:11])=[O:19])[CH2:5]1

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 1575683-Furancarboxaldehyde, tetrahydro-

생성물 1

HCID 57478039ethyl (2E)-3-(oxolan-3-yl)prop-2-enoate수율 52%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a 0° C. mixture of sodium hydride (60% in mineral oil) (382 mg, 9.40 mmol) in DMF (15.0 mL) (THF may also be used) was added triethyl phosphonoacetate (1.72 mL, 8.68 mmol) dropwise. The resulting mixture was warmed to room temperature and stirred for 30 minutes, then was re-cooled to 0° C., at which time a solution of tetrahydrofuran-3-carbaldehyde (724 mg, 7.23 mmol) in DMF (4.0 mL) was added dropwise. The resulting mixture was stirred at this temperature for 1.5 hours, at which time the mixture was diluted with water and the product was extracted with ether. The combined extracts were washed with water and brine, dried over sodium sulfate and the solvent removed in vacuo. Flash column chromatography (eluting with a gradient from 0-40% ethyl acetate in hexanes) afforded the product (640 mg, 52%).

후처리

  1. additionwas added dropwise
  2. stirringThe resulting mixture was stirred at this temperature for 1.5 hours, at which time the mixture
  3. extractionthe product was extracted with ether
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent removed in vacuo
  7. washFlash column chromatography (eluting with a gradient from 0-40% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-3991614f252c4529a4f8b0dcc2538c69
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530485B2

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