Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 3-(5-methylthiophen-2-yl)prop-2-enoate

HRID 651634ノート

反応式

HRID 651634 の反応式
[CH3:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]([CH:13]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12]>C(Cl)Cl>[CH3:9][O:10][C:11](=[O:12])[CH:13]=[CH:7][C:5]1[S:6][C:2]([CH3:1])=[CH:3][CH:4]=1

参加物

4

反応物 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 616635-Methyl-2-thiophenecarboxaldehyde

生成物 1

HCID 53641428Methyl 3-(5-methylthiophen-2-yl)prop-2-enoate収率 62.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 5-methyl-thiophene-2-carboxaldehyde (5 g, 40 mmol) in CH2Cl2 (100 mL) is added methyl (triphenylphosphoranylidene) acetate (13.3 g, 40 mmol). The solution is stirred for 72 hours. After this time, the solution is concentrated. The residue is slurried in Et2O. The solution is filtered through a bed of Celite. The collected liquid is concentrated. The residue is purified by column chromatography eluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes to give the title compound (4.5 g, 25 mmol) as an oil.

後処理

  1. concentrationAfter this time, the solution is concentrated
  2. filtrationThe solution is filtered through a bed of Celite
  3. concentrationThe collected liquid is concentrated
  4. customThe residue is purified by column chromatography
  5. washeluting with a gradient of 50% EtOAc/hexanes to 60% EtOAc/hexanes

出典と根拠

ORDレコード
ord-997cf3b78b544914ba3c89f3e3fa0ad6
出典データセット
uspto-grants-2001_08
特許番号
US06281227B1

反応ノート

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