Sulfuric Acid → HCID 19921956, compound

HRID 1648094Notes

Reaction equation

HRID 1648094 reaction equation
C([O:3][C:4](=[O:43])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O: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.[OH-].[Li+].S(=O)(=O)(O)O.C(OCC)(=O)C>O1CCCC1.O>[C:38]([CH2:37][CH2:36][C:11]1[CH:10]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:43])=[O:3])[CH:14]=[CH:13][C:12]=1[O: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 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 54300408HCID 54300408, compound

Product 1

HCID 19921956HCID 19921956, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.93 g (3.23 mmol) of 4-[[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyl]oxy]-3-(3-ethoxy-3-oxopropyl)benzenepentanoic acid ethyl ester from the preceding example, in 30 mL of tetrahydrofuran and 30 mL of water, was added 0.407 g (9.71 mmol) of lithium hydroxide monohydrate and the resulting solution was stirred at room temperature for 46 hr. The reaction mixture was acidified with 60 mL of 3N aqueous sulfuric acid, and worked-up with ethyl acetate in the usual manner. The crude product was purified by flash chromatagraphy on 500 g of silica gel, eluting with hexane-ethyl acetate (1:1) affording 1.07 g (61.0%) of the title compound as a white solid, mp 101°-104° C.

Workup

  1. customThe crude product was purified by flash chromatagraphy on 500 g of silica gel
  2. washeluting with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-d549e741d83f42f1aa3b756289cd27b3
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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