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Dichloromethane → (E)-7-(tert-butyldimethylsiloxy)-2-methylhept-2-enal

HRID 658962
ノート
印刷プレビュー

反応式

HRID 658962 の反応式
C(N(CC)CC)C.C(Cl)Cl.[O:11]([CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[C:24](\[CH3:27])/[CH2:25][OH:26])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>CS(C)=O>[O:11]([CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[C:24](\[CH3:27])/[CH:25]=[O:26])[Si:12]([C:15]([CH3:17])([CH3:18])[CH3:16])([CH3:14])[CH3:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23249620HCID 23249620、化合物

生成物 1

HCID 11402629(E)-7-(tert-butyldimethylsiloxy)-2-methylhept-2-enal収率 94.9%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

After the addition of triethylamine (36.5 ml) to a methylene chloride solution (53 ml) of Alcohol 5 (13.6 g) and cooling to 0° C., a dimethylsulfoxide solution (53 ml) of SO3-pyridine (25 g) is added thereto at 0° C. and the whole is stirred for 1.5 hours. After stirring, the resultant solution is quenched using a buffer solution (5 ml) and the organic compound is extracted three times with ethyl acetate, followed by the wash of the organic layer in a saturated saline solution and drying over anhydrous sodium sulfate. After anhydrous sodium sulfate is filtered and the solvent is distilled off under reduced pressure, the residue is separated and purified by column chromatography to produce Aldehyde 6 (12.8 g) of 94% in yield.

後処理

  1. stirringAfter stirring
  2. customthe resultant solution is quenched
  3. extractionthe organic compound is extracted three times with ethyl acetate
  4. washwash of the organic layer in a saturated saline solution
  5. dry with materialdrying over anhydrous sodium sulfate
  6. filtrationAfter anhydrous sodium sulfate is filtered
  7. distillationthe solvent is distilled off under reduced pressure
  8. customthe residue is separated
  9. custompurified by column chromatography

出典と根拠

ORDレコード
ord-48d0c6b0d6664187a66d2fbadbbec161
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
USRE043038E1

反応ノート

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