Dimethyl Sulfoxide → 3-(Tributylstannyl)prop-2-enal

HRID 1587016노트

반응식

HRID 1587016 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([Sn:15]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])/[CH:16]=[CH:17]/[CH2:18][OH:19])[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C>C(Cl)Cl.CCOCC>[CH2:24]([Sn:15]([CH2:11][CH2:12][CH2:13][CH3:14])([CH2:20][CH2:21][CH2:22][CH3:23])/[CH:16]=[CH:17]/[CH:18]=[O:19])[CH2:25][CH2:26][CH3:27]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10043273(E)-3-(tributylstannyl)prop-2-en-1-ol

생성물 1

HCID 109915673-(Tributylstannyl)prop-2-enal

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

A solution of oxalyl chloride (17.3 ml) in anhydrous methylene chloride (62 ml) is cooled to -78° C. and dimethylsulfoxide (3.7 ml) is added dropwise. The mixture is stirred for 15 minutes, E-3-tributylstannyl-2-propen-1-ol (10.7 g) in methylene chloride (26 ml) added dropwise, stirred for about 10 minutes, and triethylamine (19.4 ml) added. Stirring is stopped, the mixture allowed to warm to room temperature, then stirred for about 5 minutes, diluted with ether, and washed with water. The organic solution is dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product is purified by flash chromatography to give the desired product.

후처리

  1. stirringstirred for about 10 minutes
  2. stirringStirring
  3. stirringstirred for about 5 minutes
  4. washwashed with water
  5. dry with materialThe organic solution is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by flash chromatography

출처 및 근거

ORD 기록
ord-9ce71cc17d24431986b04545cd71cfdd
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05216015

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