2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → 3-(2-Carboxyethyl)-4-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]-gamma-oxobenzenebutanoic Acid

HRID 1648027Notes

Reaction equation

HRID 1648027 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][CH3:15].C([O:18][C:19](=[O:44])[CH2:20][CH2:21][C:22](=[O:43])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br)=[C:25]([CH2:36][CH2:37][C:38]([O:40]CC)=[O:39])[CH:24]=1)C>C(O)C.C(OCC)(=O)C>[C:38]([CH2:37][CH2:36][C:25]1[CH:24]=[C:23]([C:22](=[O:43])[CH2:21][CH2:20][C:19]([OH:44])=[O:18])[CH:28]=[CH:27][C:26]=1[O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][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][CH3:15])([OH:40])=[O:39]

Participants

4

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 540674314-[(5-Bromopentyl)oxy]-3-(3-ethoxy-3-oxopropyl)-gamma-oxobenzenebutanoic Acid Ethyl Ester

Product 1

HCID 199219653-(2-Carboxyethyl)-4-[5-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]pentyloxy]-gamma-oxobenzenebutanoic AcidYield 63.8%

Reagents, catalysts & solvents 1

HCID 21584252Ethanol ethylacetateSolvent

Procedure

Starting with 0.156 g (0.76 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, and 0.357 g (0.76 mmol) of 4-[(5-bromopentyl)oxy]-3-(3-ethoxy-3-oxopropyl)-γ-oxobenzenebutanoic acid ethyl ester, the title compound (0.237 g; 63.8% overall yield) was obtained as a white solid, mp 181.5°-184° C. (recrystallized from ethanol-ethyl acetate), using the procedure of example 22.

Sources & evidence

ORD record
ord-db214d03b0ca4291822bb5967590c65f
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

Loading…