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

HRID 1612997

Reaction equation

HRID 1612997 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 110208121-Oxo-1-furyl-7-methoxycarbonyl-4-heptyneYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fec77589ac0e4266aa815806a342106b
Source dataset
uspto-grants-1993_03
Patent number
US05191109

Linked notes

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