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

HRID 250265

반응식

HRID 250265 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7762a1bfe42649fd88919eb498952b21
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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