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

HRID 1587016ノート

反応式

HRID 1587016 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 109915673-(Tributylstannyl)prop-2-enal

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9ce71cc17d24431986b04545cd71cfdd
出典データセット
uspto-grants-1993_06
特許番号
US05216015

反応ノート

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