Methyl acetoacetate → E-methyl-5-hydroxy-3-oxo-7-tributylstannyl-6-heptenoate

HRID 1587017노트

반응식

HRID 1587017 반응식
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].C([Li])CCC.[CH2:16]([Sn:20]([CH2:29][CH2:30][CH2:31][CH3:32])([CH2:25][CH2:26][CH2:27][CH3:28])/[CH:21]=[CH:22]/[CH:23]=[O:24])[CH2:17][CH2:18][CH3:19]>O1CCCC1.CCCCCC>[CH3:10][O:9][C:3](=[O:8])[CH2:4][C:5](=[O:6])[CH2:7][CH:23]([OH:24])/[CH:22]=[CH:21]/[Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28]

참가 물질

7

반응물 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 109915673-(Tributylstannyl)prop-2-enalHCID 178418339Butyllithium

생성물 1

HCID 19759789E-methyl-5-hydroxy-3-oxo-7-tributylstannyl-6-heptenoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

A suspension of sodium hydride (1.28 g) in tetrahydrofuran (70 ml) is cooled to 0° C. and methyl acetoacetate (3.2 ml) added over about 1 minute. The mixture is stirred for about 15 minutes at 0° C., 2.5M n-butyllithium in hexane (12.3 ml) added, stirred for about 20 minutes, E-3-tributylstannylacrolein (10.0 g) in tetrahydrofuran (25 ml) added over five minutes and stirred for about 15 minutes. The mixture is quenched by slow addition of 1M hydrochloric acid, diluted with ether. The aqueous layer is back-extracted with ether and the combined organic solutions washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography in 25% ethyl acetate in hexane to give the desired product.

후처리

  1. stirringstirred for about 20 minutes
  2. stirringstirred for about 15 minutes
  3. customThe mixture is quenched by slow addition of 1M hydrochloric acid
  4. additiondiluted with ether
  5. extractionThe aqueous layer is back-extracted with ether
  6. washthe combined organic solutions washed with saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified by flash chromatography in 25% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-7f72b4dc01b441adafae659ac0bacce6
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05216015

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