4-Hexenoic acid → HCID 67754673, 화합물

HRID 1769396노트

반응식

HRID 1769396 반응식
[CH3:1][O:2][C:3]([NH:5][C:6]1[C:14]([CH2:15]/[CH:16]=[C:17](\[CH3:24])/[CH2:18][CH2:19][C:20]([O:22]C)=[O:21])=[C:13]([O:25][CH3:26])[C:12]([CH3:27])=[C:11]2[C:7]=1[C:8](=[O:28])[O:9][CH2:10]2)=[O:4].O[Li].O.C(O)(=O)CCC=CC>>[CH3:1][O:2][C:3]([NH:5][C:6]1[C:14]([CH2:15]/[CH:16]=[C:17](\[CH3:24])/[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[C:13]([O:25][CH3:26])[C:12]([CH3:27])=[C:11]2[C:7]=1[C:8](=[O:28])[O:9][CH2:10]2)=[O:4]

참가 물질

4

반응물 3

HCID 1013844-Hexenoic acidHCID 168937Lithium hydroxide, monohydrateHCID 86748395HCID 86748395, 화합물

생성물 1

HCID 67754673HCID 67754673, 화합물

실험 절차

A solution of methyl (E)-6-(1,3-dihydro-4-isocyanato-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate (1.0 g) in 10 ml methanol was heated to reflux for 4 hours and then evaporated to dryness. The residue was recrystallized from acetone/hexane to give 0.41 g of methyl (E)-6-(1,3-dihydro-4-methoxycarbonylamino-6-methoxy-7-methyl-3- oxoisobenzofuran-5-yl)-4-methyl-4-hexenoate. The ester (0.35g) and 0.05 g of LiOH-H2O in 9 ml 2:1 MeoH-H2O was heated at reflux for 4hours. The mixture was acidified, extracted with ethyl acetate, and the organic layer was dried over MgSO4. The organic layer was concentrated and the residue was further purified by silica gel chromatography (eluant 60:40:2 hexaneethyl acetate:acetic acid) to give 0.21 g of (E)-6-(1,3-dihydro-4- methoxycarbonylamino-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl. 4-hexenoic acid, mp 155°-158° C.

후처리

  1. temperatureat reflux for 4hours
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationThe organic layer was concentrated
  5. customthe residue was further purified by silica gel chromatography (eluant 60:40:2 hexaneethyl acetate:acetic acid)
  6. customto give 0.21 g of (E)-6-(1,3-dihydro-4- methoxycarbonylamino-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-4-methyl

출처 및 근거

ORD 기록
ord-333a3983f7044a91838dab429d3108a3
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05380879

반응 노트

불러오는 중…