Water → HCID 19922086, compound

HRID 1648090Notes

Reaction equation

HRID 1648090 reaction equation
C([O:3][C:4](=[O:44])[CH2:5][CH2:6][CH2:7][C:8](=[O:43])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:32]=[CH:31][C:25]3[C:26](=[O:30])[CH2:27][CH2:28][O:29][C:24]=3[C:23]=2[CH2:33][CH2:34][CH3:35])=[C:11]([CH2:36][CH2:37][C:38]([O:40]CC)=[O:39])[CH:10]=1)C.O.O.[OH-].[Li+].S(=O)(=O)(O)O>O1CCCC1.C(OCC)(=O)C>[C:38]([CH2:37][CH2:36][C:11]1[CH:10]=[C:9]([C:8](=[O:43])[CH2:7][CH2:6][CH2:5][C:4]([OH:44])=[O:3])[CH:14]=[CH:13][C:12]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:32]=[CH:31][C:25]2[C:26](=[O:30])[CH2:27][CH2:28][O:29][C:24]=2[C:23]=1[CH2:33][CH2:34][CH3:35])([OH:40])=[O:39]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 168937Lithium hydroxide, monohydrateHCID 54437780HCID 54437780, compound

Product 1

HCID 19922086HCID 19922086, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 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 at 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-b847bb352828473fb8200a60a3ca33d9
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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