4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol → Methyl 7-(4-hydroxyphenyl)-2-naphthalenecarboxylate

HRID 1693671노트

반응식

HRID 1693671 반응식
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14]2)=[CH:9][CH:8]=1)(=O)=O.CC1(C)C(C)(C)OB([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)O1>C(COC)OC.C([O-])([O-])=O.[Na+].[Na+]>[OH:37][C:34]1[CH:35]=[CH:36][C:31]([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:14]3)=[CH:9][CH:8]=2)=[CH:32][CH:33]=1

참가 물질

5

반응물 2

HCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 59264869Methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-2-naphthalenecarboxylate

생성물 1

HCID 59264877Methyl 7-(4-hydroxyphenyl)-2-naphthalenecarboxylate수율 101.8%

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매HCID 10340Sodium Carbonate용매

반응 조건

온도
70 °C

실험 절차

A solution of methyl 7-{[(trifluoromethyl)sulfonyl]oxy}-2-naphthalenecarboxylate (100 mg, 0.3 mmol), tetrakistriphenylphosphine palladium (14 mg, 0.012 mmol) and 4-(4,4,5,5-tetramethyl 1,3,2-dioxaborolan-2-yl-)phenol (79 mg, 0.36 mmol) in a mixture of dimethoxyethane (1.6 mL) and 2 M aqueous Na2CO3 (1.3 mL) was heated in a 70° C. oil bath for one hour. The solution was partitioned between ethyl acetate and water. The organic layer was dried with magnesium sulfate, filtered, and concentrated. The crude material was purified by chromatography on silica gel, (hexane to 3:7 ethyl acetate:hexanes) to provide the title compound (0.085 g, 95.5% as 0.20 ethyl acetate). 1H NMR (DMSO-d6): 9.64 (s, 1H), 8.65 (s, 1H), 8.31 (s, 1H), 8.03-7.99 (m, 2H), 7.93-7.90 (m, 2H), 7.66 (d, J=9 Hz, 2H), 6.88 (d, J=9 Hz, 2H), 3.90 (s, 3H).

후처리

  1. customThe solution was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by chromatography on silica gel, (hexane to 3:7 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-4ecbf5513dea42cebb89d3ffb59407ac
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158665B2

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