Sodium Carbonate → Methyl 6-(4-hydroxyphenyl)-1-naphthoate

HRID 645999노트

반응식

HRID 645999 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]2)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[OH:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1>COCCOC.C(OCC)(=O)C.O>[OH:29][C:30]1[CH:35]=[CH:34][C:33]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]3)=[CH:32][CH:31]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 22622428Methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate

생성물 1

HCID 59264867Methyl 6-(4-hydroxyphenyl)-1-naphthoate수율 88.3%

시약·촉매·용매 3

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of methyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthoate (271 g, 0.81 mol) (from multiple batches), tetrakis(triphenylphospine)palladium (0) (37.4 g, 0.032 mol), 2 M sodium carbonate solution (1.3 L) and 4-hydroxyphenyl boronic acid (134 g, 0.97 mol) in ethylene glycol dimethyl ether (1.5 L) was heated at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (2 L) and water (2 L). The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered and concentrated to a dark semisolid residue. The crude material was purified by crystallization from dichloromethane-heptane to give 199 g of the product as a tan solid.

후처리

  1. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated to a dark semisolid residue
  4. customThe crude material was purified by crystallization from dichloromethane-heptane

출처 및 근거

ORD 기록
ord-382534a3568140809b5caf4f4d95c772
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705028B2

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