Ethyl Acetate → 1-[3-(Cyclopentyloxy)-4-methoxyphenyl]butane-1,3-dione

HRID 2373187노트

반응식

HRID 2373187 반응식
[H-].[Na+].[C:3](OCC)(=[O:5])[CH3:4].[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([C:23](=[O:25])[CH3:24])[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:13][CH2:12][CH2:11][CH2:10]1>O1CCCC1.C(O)C.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([C:23](=[O:25])[CH2:24][C:3](=[O:5])[CH3:4])[CH:18]=[CH:19][C:20]=2[O:21][CH3:22])[CH2:10][CH2:11][CH2:12][CH2:13]1

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 117465791-(3-(Cyclopentyloxy)-4-methoxyphenyl)ethanone

생성물 1

HCID 691556961-[3-(Cyclopentyloxy)-4-methoxyphenyl]butane-1,3-dione수율 88.3%

시약·촉매·용매 3

HCID 702Ethanol촉매HCID 26541Dibenzo-18-crown-6촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a stirred suspension of 60% sodium hydride (200 mg, 5 mmol) and ethyl acetate (0.49 ml, 5 mmol) in tetrahydrofuran (25 ml) were sequentially added a solution of 1-[3-(cyclopentyloxy)-4-methoxyphenyl]ethanone (European Patent Application EP470805) (590 mg, 2.5 mmol) in tetrahydrofuran (5 ml), two drops of ethanol and a solution of dibenzo-18-crown (15 mg, 0.04 mmol) in tetrahydrofuran (5 ml). The reaction mixture was refluxed for 5 h, allowed to cool to room temperature and finally quenched with aqueous 10% sulphuric acid solution (5 ml). The resulting mixture was diluted with diethyl ether, washed with saturated ammonium chloride solution, dried and concentrated under reduced pressure to yield a crude product which was purified by column chromatography (SiO2, hexane-ethyl acetate 4:1) to afford the title compound (610 mg, 86% yield) as a pale yellow oil.

후처리

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. customfinally quenched with aqueous 10% sulphuric acid solution (5 ml)
  3. additionThe resulting mixture was diluted with diethyl ether
  4. washwashed with saturated ammonium chloride solution
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customto yield a crude product which
  8. customwas purified by column chromatography (SiO2, hexane-ethyl acetate 4:1)

출처 및 근거

ORD 기록
ord-766344241a814ed3bcfbe98fe1bd86ee
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07459453B2

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