Lithium Hydroxide → 2-[(5-Carboxypentyl)oxy]-6-[6-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl]oxy]hexyl]benzenepropanoic Acid

HRID 1648085Notes

Reaction equation

HRID 1648085 reaction equation
C[O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:39]=[CH:38][C:32]2[C:33](=[O:37])[CH2:34][CH2:35][O:36][C:31]=2[C:30]=1[CH2:40][CH2:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[OH-].[Li+]>O1CCCC1>[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:39]=[CH:38][C:32]3[C:33](=[O:37])[CH2:34][CH2:35][O:36][C:31]=3[C:30]=2[CH2:40][CH2:41][CH2:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:6]=1[CH2:5][CH2:4][C:3]([OH:49])=[O:2])([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 541968202-[6-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl)oxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic acid methyl ester

Product 1

HCID 199219052-[(5-Carboxypentyl)oxy]-6-[6-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl]oxy]hexyl]benzenepropanoic AcidYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 2-[6-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl]oxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic acid methyl ester from the preceding example (0.38 g; 0.565 mmol) was saponified by stirring with 2 mL of 3N aqueous lithium hydroxide, in 15 mL of tetrahydrofuran for 24 hr, at room temperature. Work-up as in example 4 followed by flash-chromatography on silica gel (eluting with 96:3:1 chloroform-methanol-acetic acid) and recrystallization from hexane-ethyl acetate gave 0.36 g (98%) of the title compound as a colorless solid, mp 97°-98° C.

Workup

  1. customfollowed by flash-chromatography on silica gel (eluting with 96:3:1 chloroform-methanol-acetic acid) and recrystallization from hexane-ethyl acetate

Sources & evidence

ORD record
ord-a67aa3a920e24e3ca059b8cbfb22ad9b
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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