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

HRID 1432871ノート

反応式

HRID 1432871 の反応式
[Cl:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.C1(P(=[CH:28][C:29]([O:31][CH3:32])=[O:30])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[CH3:32][O:31][C:29](=[O:30])/[CH:28]=[CH:7]/[C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1

参加物

4

反応物 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 817002-Thiophenecarboxaldehyde, 5-chloro-

生成物 1

HCID 69024911Methyl 3-(5-chlorothiophen-2-yl)prop-2-enoate収率 87.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-chloro-2-thiophene-carboxaldehyde (5.10 g, 34.8 mmol) in 100 mL of dry CH2Cl2 is added methyl (triphenylphosphoranylidene)acetate (11.8 g, 35.3 mmol). The resulting brown-green mixture is stirred for 19 h at room temperature. The mixture is filtered through a Celite pad, concentrated in vacuo and triturated with hexane. The white precipitate (triphenylphosphine oxide) is filtered off and the filtrate is concentrated. The crude residue is purified via flash column chromatography eluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes to provide the title compound (6.20 g, 30.6 mmol) as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ7.65 (d, 1H), 7.05 (d, 1H), 6.89 (d, 1H), 6.10 (d, 1H), 3.80 (s, 3H).

後処理

  1. filtrationThe mixture is filtered through a Celite pad
  2. concentrationconcentrated in vacuo
  3. customtriturated with hexane
  4. filtrationThe white precipitate (triphenylphosphine oxide) is filtered off
  5. concentrationthe filtrate is concentrated
  6. customThe crude residue is purified via flash column chromatography
  7. washeluting with a gradient of 5% EtOAc/hexanes to 10% EtOAc/hexanes

出典と根拠

ORDレコード
ord-c9c57ca99b3f45578bf5728c533a3cc4
出典データセット
uspto-grants-2009_11
特許番号
US07612075B2

反応ノート

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