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Sodium Iodide → HCID 14329880, 화합물

HRID 2232478
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HRID 2232478 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 1

HCID 14329880HCID 14329880, 화합물수율 68.9%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

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 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.

후처리

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

출처 및 근거

ORD 기록
ord-7b9bdafba6a94ff08869ebb27ca87efa
출처 데이터셋
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04788214

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