Lithium hydroxide, monohydrate → HCID 15595186, compound

HRID 1906214Notes

Reaction equation

HRID 1906214 reaction equation
C[O:2][C:3](=[O:38])[CH2:4][O:5][C:6]1[CH:34]=[CH:33][C:9]2[C:10](=[O:32])[CH2:11][CH:12]([CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[C:21]([OH:28])[C:20]=3[CH2:29][CH2:30][CH3:31])[O:13][C:8]=2[C:7]=1[CH2:35][CH2:36][CH3:37].O.[OH-].[Li+]>O.O1CCCC1.O>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:12]2[CH2:11][C:10](=[O:32])[C:9]3[CH:33]=[CH:34][C:6]([O:5][CH2:4][C:3]([OH:38])=[O:2])=[C:7]([CH2:35][CH2:36][CH3:37])[C:8]=3[O:13]2)=[C:20]([CH2:29][CH2:30][CH3:31])[C:21]=1[OH:28])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57164760HCID 57164760, compound

Product 1

HCID 15595186HCID 15595186, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 0.3 g of the ester product from Example 17 and 0.48 g of lithium hydroxide monohydrate in 10 ml of 1:1 water-tetrahydrofuran was stirred at room temperature for 24 hours then diluted with water and extracted with ether (the ether extract was discarded). The aqueous solution was acidified with 1N hydrochloric acid and extracted 3 times with ether. The ether extracts were combined, dried (magnesium sulfate), filtered and concentrated in vacuo giving a solid residue which was chromatographed on 12 g of silica gel. Elution with tetrahydrofuran gave the acid which was recrystallized from methanol yielding rac.-[[2-[4-(4-acetyl-3-hydroxy-2-propylphenoxy)butyl]-3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl]oxy]acetic acid as an off-white solid, m.p. 163.5°-167.0° C.

Workup

  1. extractionextracted with ether (the ether
  2. extractionextract
  3. extractionextracted 3 times with ether
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customgiving a solid residue which
  8. customwas chromatographed on 12 g of silica gel
  9. washElution with tetrahydrofuran
  10. customgave the acid which
  11. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-cebe274d0f8546128d4bf28afc78feda
Source dataset
uspto-grants-1987_03
Patent number
US04650812

Reaction notes

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