Acrylic Acid → 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid

HRID 1839862노트

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HRID 1839862 반응식
[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]

참가 물질

4

반응물 3

HCID 6581Acrylic AcidHCID 8029FuranHCID 425307Triacetyl borate

생성물 1

HCID 31593757-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid수율 43%

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온도
-5 °C

실험 절차

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).

후처리

  1. additionwere charged in a similar reactor as in Example 4
  2. filtrationThe resulting crystals were collected by filtration through a glass
  3. filtrationfilter
  4. washwashed with diisopropyl ether (60 ml)
  5. temperaturecooled to not more than 5° C.
  6. customdried under reduced pressure for 2 hr

출처 및 근거

ORD 기록
ord-90c4e97521504885a38bbee33eaa43d4
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677464B2

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