HCID 15296555, compound → 2-[[5-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl]oxy]pentyl]oxy]benzenepropanoic acid methyl ester

HRID 328023Notes

Reaction equation

HRID 328023 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:22][O:23][C:24](=[O:44])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]OS(C)(=O)=O>>[CH3:22][O:23][C:24](=[O:44])[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][O:1][C:2]1[CH:12]=[CH:11][C:5]2[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 15296555HCID 15296555, compoundHCID 541680372-[[5-[(Methylsulfonyl)oxy]pentyl]oxy]benzenepropanoic Acid Methyl Ester

Product 1

HCID 542382182-[[5-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl]oxy]pentyl]oxy]benzenepropanoic acid methyl esterYield 75.5%

Procedure

Using the procedure of example 11 and starting with 1.13 g (4 mmol) of 2,3-dihydro-7-hydroxy-8-(3-phenylpropyl)-4H-1-benzopyran-4-one (from example 194) and 1.38 g (4 mmol) of 2-[[5-[(methylsulfonyl)oxy]pentyl]oxy]benzenepropanoic acid methyl ester (from example 72), 2-[[5-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl]oxy]pentyl]oxy]benzenepropanoic acid methyl ester was obtained in 75.5% yield (1.6 g) as a pale-yellow oil. This diester (3 mmol) was saponified with 13.6 mL of 3N aqueous lithium hydroxide in 80 mL of tetrahydrofuran, at room temperature, for 96 hr. Work-up as in example 4 and recrystallization from ethyl acetate gave 0.6 g (38.5%) of the title acid, a colorless solid, mp 98°-99° C.

Sources & evidence

ORD record
ord-a605640b072b4e998ce7cc8811fd9f92
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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