4-Hexenoic acid → HCID 67754673, compound

HRID 1769396Notes

Reaction equation

HRID 1769396 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

HCID 67754673HCID 67754673, compound

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-333a3983f7044a91838dab429d3108a3
Source dataset
uspto-grants-1995_01
Patent number
US05380879

Reaction notes

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