Sulfuric Acid → HCID 19922128, compound

HRID 1648101Notes

Reaction equation

HRID 1648101 reaction equation
C([O:3][C:4](=[O:45])[CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:18][C:19]([O:21]CC)=[O:20])[CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]1[CH:41]=[CH:40][C:34]2[C:35](=[O:39])[CH2:36][CH2:37][O:38][C:33]=2[C:32]=1[CH2:42][CH2:43][CH3:44])C.O.[OH-].[Li+].S(=O)(=O)(O)O>C(OCC)(=O)C.O.O1CCCC1>[C:19]([CH2:18][O:17][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[CH:9][C:8]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30][C:31]3[CH:41]=[CH:40][C:34]4[C:35](=[O:39])[CH2:36][CH2:37][O:38][C:33]=4[C:32]=3[CH2:42][CH2:43][CH3:44])=[C:7]2[CH2:6][CH2:5][C:4]([OH:45])=[O:3])=[CH:12][CH:13]=1)([OH:21])=[O:20]

Participants

7

Reactant 3

HCID 1118Sulfuric AcidHCID 168937Lithium hydroxide, monohydrate2×HCID 53779795HCID 53779795, compound

Product 1

HCID 19922128HCID 19922128, compoundYield 102.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.86 g (1.39 mmol) of 2-[[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]oxy]-7-(2-ethoxy-2-oxoethoxy)-1-naphthalenepropanoic acid ethyl ester from the preceding example, 0.177 g (4.21 mmol) of lithium hydroxide monohydrate, 10.1 mL of tetrahydrofuran, and 10.1 mL of water was stirred at room temperature for 41.5 hr. A second saponification was carried out with 0.188 g (0.3 mmol) of the starting ester, 38 mg (0.9 mmol) of lithium hydroxide monohydrate, 2.2 mL of tetrahydrofuran and 2.2 mL of water. After combining the two reaction mixtures, 30 mL of 3N aqueous sulfuric acid was added, and the mixture was worked-up with ethyl acetate in the usual manner. The crude product was crystallized from hexane-ethyl acetate to give 0.803 g (84.3%) of the title compound as an off-white solid, mp 175°-177.5° C.

Workup

  1. additionwas added
  2. customThe crude product was crystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-bd5b1990e5c94923b8fbe21194008719
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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