Water → HCID 19922086, compound

HRID 328030Notes

Reaction equation

HRID 328030 reaction equation
C([O:3][C:4](=[O:23])[CH2:5][CH2:6][CH2:7][C:8](=[O:22])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][C:17]([O:19]CC)=[O:18])[CH:10]=1)C.[OH2:24].[OH2:25].[OH-].[Li+].S(=O)(=O)(O)O.[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>C(OCC)(=O)C>[C:17]([CH2:16][CH2:15][C:11]1[CH:10]=[C:9]([C:8](=[O:22])[CH2:7][CH2:6][CH2:5][C:4]([OH:3])=[O:23])[CH:14]=[CH:13][C:12]=1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:14][CH2:13][O:24][C:35]1[CH:34]=[CH:4][C:5]2[C:6](=[O:25])[CH2:7][CH2:8][O:33][C:37]=2[C:36]=1[CH2:15][CH2:16][CH3:17])([OH:19])=[O:18]

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86747457HCID 86747457, compound

Product 1

HCID 19922086HCID 19922086, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.442 g (0.73 mmol) of 4-[6-[3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]hexyl]-3-(3-ethoxy-3-oxopropyl)-δ-oxobenzenepentanoic acid ethyl ester from the preceding example, in 7 mL of tetrahydrofuran and 7 mL of water was added 91.7 mg (2.19 mmol) of lithium hydroxide monohydrate and the reaction was stirred for room temperature for 19.3 hr. After being acidified with 16 mL of 3N aqueous sulfuric acid, the mixture was worked-up with ethyl acetate in the usual manner. The crude product thus obtained was recrystallized from hexane-ethyl acetate to give 0.309 g (77%) of the title compound as a white solid, mp 136°-139° C.

Workup

  1. customThe crude product thus obtained
  2. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-4f6c296025914207873fb22206922a84
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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