2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one → HCID 19921934, compound

HRID 328018Notes

Reaction equation

HRID 328018 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:51])[CH2:19][CH2:20][C:21]1[C:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]OS(C)(=O)=O)=[CH:25][CH:24]=[CH:23][C:22]=1[O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][C:47]([O:49]C)=[O:48]>>[C:47]([CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:38][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][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])[C:21]=1[CH2:20][CH2:19][C:18]([OH:51])=[O:17])([OH:49])=[O:48]

Participants

3

Reactant 2

HCID 153182992,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-oneHCID 54277518HCID 54277518, compound

Product 1

HCID 19921934HCID 19921934, compound

Procedure

Using the procedure of example 184, the title compound was prepared in 47% overall yield by alkylation of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one with 2-[(9-methoxy-9-oxononyl)oxy]-6-[6-[(methylsulfonyl)oxy]hexyl]benzenepropanoic acid methyl ester from the preceding example followed by saponification. The diacid product was a colorless solid, mp 63°-65° C., recrystallized from hexane-ethyl acetate.

Workup

  1. customrecrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ce1d88465fde44329180dae15fa6fcfe
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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