HCID 86750893, compound → HCID 54488078, compound

HRID 1781549Notes

Reaction equation

HRID 1781549 reaction equation
CC(N)C1C=CC=CC=1.[OH:10][C:11]1[C:19]([CH2:20][CH:21]=[C:22]([CH3:29])[CH2:23][CH:24]([CH3:28])[C:25]([OH:27])=[O:26])=[C:18]([O:30][CH3:31])[C:17]([CH3:32])=[C:16]2[C:12]=1[C:13](=[O:33])[O:14][CH2:15]2>C(OCC)(=O)C.CCCCCC>[OH:10][C:11]1[C:19]([CH2:20][CH:21]=[C:22]([CH3:29])[CH2:23][CH:24]([CH3:28])[C:25]([OH:27])=[O:26])=[C:18]([O:30][CH3:31])[C:17]([CH3:32])=[C:16]2[C:12]=1[C:13](=[O:33])[O:14][CH2:15]2

Participants

4

Reactant 1

HCID 86750893HCID 86750893, compound

Product 1

HCID 54488078HCID 54488078, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl -3-oxoisobenzofuran-5-yl)-2,4-dimethyl-4-hexenoic acid (+)-α-Methylbenzylamine Salt (380 g, 0.84 mol) in ethyl acetate (0.75L) and hexane (0.1L) was washed with 2M sulfuric acid (0.5L, then 2×0.25L) and water (0.2L). The clear organic layer was dried over sodium sulfate, filtered and heated to reflux. Hexane (1.4L) was added and upon cooling the product crystallized. An additional portion of hexane (0.8L) was added and after cooling in ice the product was collected by filtration and dried to afford (S) (E) 6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisobenzofuran -5-yl)-2,4-dimethyl-4-hexenoic acid, m.p. 122°-123° C.

Workup

  1. washwas washed with 2M sulfuric acid (0.5L
  2. dry with materialThe clear organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. temperatureheated to reflux
  5. additionHexane (1.4L) was added
  6. temperatureupon cooling the product
  7. customcrystallized
  8. additionAn additional portion of hexane (0.8L) was added
  9. temperatureafter cooling in ice the product
  10. filtrationwas collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-faa12b73e2ce459d9ce97a9173186125
Source dataset
uspto-grants-1997_05
Patent number
US05633279

Reaction notes

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