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

HRID 1612989

Reaction equation

HRID 1612989 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 64.9%

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 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.

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. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-93aeac72e4534a92a314f91698ab32c5
Source dataset
uspto-grants-1993_03
Patent number
US05191109

Linked notes

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