Acrylic Acid → 7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
Reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[C:6]([O:9]B(OC(=O)C)OC(=O)C)(=[O:8])C.[C:19](O)(=O)[CH:20]=C>>[CH:5]12[O:1][CH:2]([CH:19]=[CH:20]1)[CH2:3][CH:4]2[C:6]([OH:9])=[O:8]Participants
4
Conditions
- Temperature
- -5 °C
Procedure
Distilled furan (141.7 g, 2.08 mol) and triacetoxyborane (1.19 g, 6.63 mmol) were charged in a similar reactor as in Example 4, and the mixture was cooled to −5° C. To this mixed solution was added acrylic acid (30.4 g, 0.42 mol) and the mixture was stirred at an inner temperature of −5° C. for 22 hr. The resulting crystals were collected by filtration through a glass filter, washed with diisopropyl ether (60 ml) cooled to not more than 5° C. and dried under reduced pressure for 2 hr. to give 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid as colorless crystals (11.4 g, endo form:exo form=98:2, purity >99%, yield 43% based on acrylic acid).
Workup
- additionwere charged in a similar reactor as in Example 4
- filtrationThe resulting crystals were collected by filtration through a glass
- filtrationfilter
- washwashed with diisopropyl ether (60 ml)
- temperaturecooled to not more than 5° C.
- customdried under reduced pressure for 2 hr
Sources & evidence
- ORD record
- ord-90c4e97521504885a38bbee33eaa43d4
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06677464B2
Reaction notes
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