Dimethyl Sulfoxide → trans-2-(4-Bromophenyl)cyclopropane-1-carbaldehyde

HRID 73297

反応式

HRID 73297 の反応式
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:20][C@@H:19]2[CH2:21][OH:22])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C@H:18]2[CH2:20][C@@H:19]2[CH:21]=[O:22])=[CH:16][CH:17]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57515373((1S,2S)-2-(4-bromophenyl)cyclopropyl)methanol

生成物 1

HCID 57515374trans-2-(4-Bromophenyl)cyclopropane-1-carbaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

DMSO (3 equivalents) was added dropwise to a solution of oxalyl chloride in anhydrous dichloromethane under N2 at −78° C. A solution of the alcohol from Example 28B ((1S,2S)-[2-(4-bromophenyl)cyclopropyl]methanol) in dichloromethane was then added dropwise at −78° C. Stirring at this temperature was continued for 30 minutes, then triethylamine (4 equivalents) was added and the dry ice bath was removed. After stirring for 1 hour, the mixture was treated with saturated aqueous NH4Cl. The mixture was extracted with ether. The combined organic extracts was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by eluting through a pad of silica gel with hexane to provide the title compound.

後処理

  1. customthe dry ice bath was removed
  2. stirringAfter stirring for 1 hour
  3. additionthe mixture was treated with saturated aqueous NH4Cl
  4. extractionThe mixture was extracted with ether
  5. dry with materialThe combined organic extracts was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified
  9. washby eluting through a pad of silica gel with hexane

出典と根拠

ORDレコード
ord-085b4b5b2e29468f94533ee31bb0c49e
出典データセット
uspto-grants-2014_09
特許番号
US08829041B2

関連ノート

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