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

HRID 1612989

반응식

HRID 1612989 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 110208121-Oxo-1-furyl-7-methoxycarbonyl-4-heptyne수율 64.9%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-93aeac72e4534a92a314f91698ab32c5
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05191109

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