Sodium Iodide → HCID 14329880, compound

HRID 2231897Notes

Reaction equation

HRID 2231897 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH2:8][CH2:7][C:6]=2[CH:15]=1.Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[CH3:28])=[C:23]([OH:30])[C:22]=1[CH2:31][CH2:32][CH3:33].[H-].[Na+].[I-].[Na+]>CN(C)C=O>[C:27]([C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH2:18][CH2:17][O:1][C:2]2[CH:3]=[CH:4][C:5]3[O:10][C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH2:8][CH2:7][C:6]=3[CH:15]=2)=[C:22]([CH2:31][CH2:32][CH3:33])[C:23]=1[OH:30])(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 189965446-Hydroxy-2-methyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

Product 1

HCID 14329880HCID 14329880, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The procedure of Example 7 was employed to alkylate 0.9 g of the ethyl ester of racemic-3,4-dihydro-6-hydroxy-2-methyl-2H-1-benzopyran-2-carboxylic acid with 4'-(3-bromopropoxy)-2'-hydroxy-3'-n-propylacetophenone (1.5 g), using sodium hydride (12.16 mmole), and sodium iodide (10 mmoles), in N,N-dimethylformamide. After saponification with lithium hydroxide monohydrate (1.5 g), the crude acid product was purified by chromatography on silica gel. There was obtained 1.16 g (68.9%) of racemic-6-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3,4-dihydro-2-methyl-2H-1-benzopyran-2-carboxylic acid as an off-white solid mp 108°-110.5° C.

Workup

  1. customAfter saponification with lithium hydroxide monohydrate (1.5 g), the crude acid product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-97c8162cb1f54c67aa41d776a9503b24
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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