Dimethyl Sulfoxide → 1-Allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)azetidine

HRID 1650295ノート

反応式

HRID 1650295 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:14][C:15]([N:17]1[CH2:20][CH:19]([CH2:21]O)[CH2:18]1)=[O:16])[CH:12]=[CH2:13].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[C:30]([CH3:34])[C:31](=[O:33])[CH3:32])C=CC=CC=1>C(Cl)Cl.O.C(N(CC)CC)C>[CH2:11]([O:14][C:15]([N:17]1[CH2:18][CH:19]([CH:21]=[C:30]([CH3:34])[C:31](=[O:33])[CH3:32])[CH2:20]1)=[O:16])[CH:12]=[CH2:13]

参加物

8

反応物 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 3019223-(Triphenyl-lambda~5~-phosphanylidene)butan-2-oneHCID 199148921-Allyloxycarbonyl-3-hydroxymethylazetidine

生成物 1

HCID 570666331-Allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)azetidine収率 89.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒3 回HCID 8471Triethylamine溶媒

実験手順

To a solution of oxalyl chloride (6.3 g) in methylene chloride (85 ml) was added dimethyl sulfoxide (3.87 g) at -60° C. and stirred was stirred for 15 minutes. A solution of 1-allyloxycarbonyl-3-hydroxymethylazetidine (6.8 g) in methylene chloride (21 ml) was then added thereto and the mixture was stirred at -60° C. for 30 minutes. Triethylamine (20 g) was dropwise added thereto. To the mixture was added water (50 ml) and organic layer was separated washed with water, dried over magnesium sulfate, evaporated and coevaporated with benzene to give an oily residue. The residue was dissolved in methylene chloride (160 ml) and 3-triphenylphosphoranylidenebutan-2-one (11.8 g) was added thereto and the mixture was stirred overnight at room temperature. The evaporated residue was triturated with ethyl acetate and the insoluble material was filtered. The filtrate was applied on silica gel column using a mixture of n-hexane and ethyl acetate. The main fractions were evaporated to give 1-allyloxycarbonyl-3-(2-methyl-3-oxo-1-butenyl)azetidine (7.06 g).

後処理

  1. stirringwas stirred for 15 minutes
  2. stirringthe mixture was stirred at -60° C. for 30 minutes
  3. customwas separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customto give an oily residue
  8. stirringthe mixture was stirred overnight at room temperature
  9. customThe evaporated residue was triturated with ethyl acetate
  10. filtrationthe insoluble material was filtered
  11. additiona mixture of n-hexane and ethyl acetate
  12. customThe main fractions were evaporated

出典と根拠

ORDレコード
ord-5fd7cdcf94a44771aaf6a41bff81e2b7
出典データセット
uspto-grants-1990_05
特許番号
US04923857

反応ノート

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