Dimethyl acetylenedicarboxylate → HCID 13052426, compound

HRID 1702536Notes

Reaction equation

HRID 1702536 reaction equation
[C:1]1([CH2:7][C:8]2[O:12][CH:11]=[C:10]([CH2:13][OH:14])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([C:21]([O:23][CH3:24])=[O:22])#[C:16][C:17]([O:19][CH3:20])=[O:18]>C1(C)C=CC=CC=1>[CH3:20][O:19][C:17]([C:16]1[CH:11]2[O:12][C:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:15]=1[C:21]([O:23][CH3:24])=[O:22])[CH:9]=[C:10]2[CH2:13][OH:14])=[O:18]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 123643963-Furanmethanol, 5-(phenylmethyl)-

Product 1

HCID 13052426HCID 13052426, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 5.6 grams (0.03 mole) of [5-(phenylmethyl)-3-furanyl]methanol and 4.3 grams (0.03 mole) of dimethyl acetylenedicarboxylate in 100 ml of toluene was heated under reflux for 3 hours. The solvent was removed under reduced pressure to give approximately 10 grams of 2,3-bis(methoxycarbonyl)-4-phenylmethyl-7-oxabicyclo[2.2.1]hepta-2,5-diene-6-methanol. The alcohol was used without further purification.

Workup

  1. temperatureunder reflux for 3 hours
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d832efdb38784bef94f711dfd9acbfae
Source dataset
uspto-grants-1982_09
Patent number
US04348326

Reaction notes

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