2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19922136, compound

HRID 1648068Notes

Reaction equation

HRID 1648068 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:17][C:18](=[O:47])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]OS(C)(=O)=O)[C:25]=1[CH2:41][CH2:42][C:43]([O:45]C)=[O:44]>>[C:43]([CH2:42][CH2:41][C:25]1[C:26]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:1][C:2]2[CH:12]=[CH:11][C:5]3[C:6](=[O:10])[CH2:7][CH2:8][O:9][C:4]=3[C:3]=2[CH2:13][CH2:14][CH3:15])=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:18]([OH:47])=[O:17])([OH:45])=[O:44]

Participants

3

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 54182027HCID 54182027, compound

Product 1

HCID 19922136HCID 19922136, compound

Procedure

Using the procedure of example 126, 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one was converted into the title compound by alkylation with 2-(3-methoxy-3-oxopropyl)-3-[6-[(methylsulfonyl)oxy]hexyl]benzenehexanoic acid methyl ester from the preceding example, followed by saponification, in 16.8% overall yield. The product was a colorless solid, mp 109°-110° C., recrystallized from acetonitrile.

Sources & evidence

ORD record
ord-2eac43db9cff4893a759138c2dc4faef
Source dataset
uspto-grants-1995_07
Patent number
US05434186

Reaction notes

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