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Water → 4-Methyl-3-thiopheneboronic acid

HRID 1432570
ノート
印刷プレビュー

反応式

HRID 1432570 の反応式
CC1(C)C(C)(C)[O:5][B:4]([C:9]2[C:13]([CH3:14])=[CH:12][S:11][CH:10]=2)[O:3]1.O>CC(C)=O>[CH3:14][C:13]1[C:9]([B:4]([OH:5])[OH:3])=[CH:10][S:11][CH:12]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 962WaterHCID 162183474,4,5,5-Tetramethyl-2-(4-methylthiophen-3-yl)-1,3,2-dioxaborolane

生成物 1

HCID 50839314-Methyl-3-thiopheneboronic acid収率 35.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 4,4,5,5-tetramethyl-2-(4-methyl-thiophen-3-yl)-[1,3,2]dioxaborolane (3.69 g, 16.47 mmol) in acetone (30 mL) is treated with H2O (30 mL), followed by NaIO4 (7.05 g, 32.95 mmol). The resulting mixture is stirred at rt overnight. The organic solvent is removed in vacuo. The residue is diluted with H2O (50 mL), extracted with EtOAc ((2×100 mL). The organic extracts are combined, dried with Na2SO4, filtered and concentrated. Purification of the crude material by chromatography gives the title compound (0.82 g, 5.78 mmol, 35%). 1H NMR (CDCl3): δ 1.33 (s, 3H), 2.64-2.66 (m, 2H), 7.00-7.02 (m, 1H), 8.27 (d, J=3.0 Hz, 1H). ES-MS (m/z): calcd for C5H7BO2S (M−H)−: 141.0; found: 141.1.

後処理

  1. customThe organic solvent is removed in vacuo
  2. additionThe residue is diluted with H2O (50 mL)
  3. extractionextracted with EtOAc ((2×100 mL)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the crude material by chromatography

出典と根拠

ORDレコード
ord-a8a30ceb476343bbae7eb70893bc2549
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07612067B2

反応ノート

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