Furan → 1-Oxo-1-furyl-7-methoxycarbonyl-4-heptyne

HRID 1612997

反応式

HRID 1612997 の反応式
[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]#[C:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:4].[O:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.ClC(Cl)C(OC(=O)C(Cl)Cl)=O>C1(C)C=CC=CC=1>[O:13]=[C:11]([C:15]1[O:14][CH:18]=[CH:17][CH:16]=1)[CH2:10][CH2:9][C:8]#[C:7][CH2:6][CH2:5][C:3]([O:2][CH3:1])=[O:4]

参加物

5

反応物 3

HCID 8029FuranHCID 77772Acetic acid, 2,2-dichloro-, 1,1'-anhydrideHCID 109761516-Methoxycarbonyl-1-carboxy-3-hexyne

生成物 1

HCID 110208121-Oxo-1-furyl-7-methoxycarbonyl-4-heptyne収率 65%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 6-methoxycarbonyl-1-carboxy-3-hexyne [VI-1] (18.4 g, 0.1 mole), furan (13.6 g, 0.2 mole), dichloroacetic anhydride (28.8 g, 0.12 mole), boron trifluoride ether complex (3.2 g) and toluene (100 ml) is reacted at 20°-30° C. for 10 hours. After completion of the reaction, the reaction mixture is cooled, washed successively with water, 5% aqueous sodium carbonate solution and water, and the organic layer is dried over anhydrous magnesium sulfate. The dried organic layer is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give 1-oxo-1-furyl-7-methoxycarbonyl-4-heptyne [VII-1] (15.2 g, yield; 65%), b.p. 120°-125° C./0.8 mmHg.

後処理

  1. customis reacted at 20°-30° C. for 10 hours
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture is cooled
  4. washwashed successively with water, 5% aqueous sodium carbonate solution and water
  5. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  6. concentrationThe dried organic layer is concentrated under reduced pressure
  7. customthe resulting residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fec77589ac0e4266aa815806a342106b
出典データセット
uspto-grants-1993_03
特許番号
US05191109

関連ノート

読み込み中…