Ethyl 6-bromo-1-benzothiophene-2-carboxylate → (6-Bromo-1-benzothiophen-2-yl)methanol

HRID 250265

反応式

HRID 250265 の反応式
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([Br:15])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=O)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Br:15][C:12]1[CH:13]=[CH:14][C:8]2[CH:7]=[C:6]([CH2:4][OH:3])[S:10][C:9]=2[CH:11]=1

参加物

4

反応物 2

HCID 13567982Ethyl 6-bromo-1-benzothiophene-2-carboxylateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 13567983(6-Bromo-1-benzothiophen-2-yl)methanol収率 60%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A −78° C. solution of 6-bromo-benzo[b]thiophene-2-carboxylic acid ethyl ester (5.75 g; 20.2 mmol) in THF (200 mL) is treated with diisobutylaluminum hydride (50.4 mL; 1.0 M) dropwise. The mixture is stirred at 0° C. for 10 minutes and quenched with HCl (1 M, 50 mL). The mixture is extracted with EtOAc (150 mL). The organic layer is dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified via flash chromatography eluting with 25% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (2.92 g, 60%). 1H NMR (400 MHz, CDCl3): δ 7.95 (s, 1H), 7.68 (d, 1H), 7.42 (d, 1H), 7.18 (s, 1H), 4.90 (s, 2H).

後処理

  1. customquenched with HCl (1 M, 50 mL)
  2. extractionThe mixture is extracted with EtOAc (150 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified via flash chromatography
  7. washeluting with 25% EtOAc/Hexanes
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-7762a1bfe42649fd88919eb498952b21
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

関連ノート

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