Furan → 3-(4-Methoxyphenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[O:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH:12]2[CH:21]3[O:17][CH:18]([CH:19]=[CH:20]3)[CH:13]2[C:14]([OH:16])=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 55 °C
Procedure
3-(4-Methoxyphenylsulfonyl)propenoic acid (200 mgs), excess furan (5.0 ml), and dry toluene (5.0 ml) were combined and warmed to 55° C. (at which time starting material went into solution) for overnight. The cooled reaction was concentrated in vacuo to a tan solid which was a mixture of starting material and product. The material was taken up in toluene (5 ml) and furan (10 ml) and heated to 69° C. overnight. The cooled reaction mixture was concentrated in vacuo to give 251 mgs of crude 3-(4-Methoxyphenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid as a dark tan solid.
Workup
- customThe cooled reaction
- concentrationwas concentrated in vacuo to a tan solid which
- additiona mixture of starting material and product
- temperaturefuran (10 ml) and heated to 69° C. overnight
- customThe cooled reaction mixture
- concentrationwas concentrated in vacuo
Sources & evidence
- ORD record
- ord-ebef189ef64f4363ad57cc24d98b5e7e
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06077864
Reaction notes
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