Acetone → 2-Methylthiophene-3-boronic acid

HRID 1432630

반응식

HRID 1432630 반응식
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[CH:13]=[CH:12][S:11][C:10]=2[CH3:14])[O:3]1.CC(C)=O>O>[CH3:14][C:10]1[S:11][CH:12]=[CH:13][C:9]=1[B:4]([OH:5])[OH:3]

참가 물질

4

반응물 2

HCID 180AcetoneHCID 455881264,4,5,5-Tetramethyl-2-(2-methylthiophen-3-yl)-1,3,2-dioxaborolane

생성물 1

HCID 218846302-Methylthiophene-3-boronic acid수율 81%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of 4,4,5,5-tetramethyl-2-(2-methyl-thiophen-3-yl)-[1,3,2]dioxaborolane (1.52 g, 6.78 mmol), acetone (15 mL) and water (15 mL) is added NaIO4 (2.90 g, 13.56 mmol). The solution is stirred at ambient temperature for 24 hours, then heated to a reflux for 24 hours. The solution is concentrated dissolved in EtOAc (1450 mL), washed with water (100 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (0.75 g, 5.49 mmol, 78%). 1H NMR (CDCl3), δ 2.93 (s, 3H), 7.10 (d, J=5.3 Hz, 1H), 7.51 (d, 5.3 Hz, 1H).

후처리

  1. temperatureheated to
  2. temperaturea reflux for 24 hours
  3. concentrationThe solution is concentrated
  4. dissolutiondissolved in EtOAc (1450 mL)
  5. washwashed with water (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-55ac376d1b1e43539ef6a69a9c74b65d
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612067B2

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