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

HRID 1612989

反応式

HRID 1612989 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 64.9%

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 and washed successively with water, 5% aqueous sodium carbonate solution and water. The organic layer is dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography to give 1-oxo-1-furyl-7-methoxycarbonyl-4-heptyne [VII-1] (15.2 g), b.p. 120°-125° C./0.3 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. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-93aeac72e4534a92a314f91698ab32c5
出典データセット
uspto-grants-1993_03
特許番号
US05191109

関連ノート

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