Acetic Anhydride → 2-Methylbenzofuran-6-yl acetate

HRID 2261830노트

반응식

HRID 2261830 반응식
COC1[CH:12]=[CH:11][C:6]2[CH:7]=[C:8]([CH3:10])[O:9][C:5]=2C=1.B(Br)(Br)Br.C(N(CC)CC)C.[C:24]([O:27][C:28](=O)[CH3:29])(=[O:26])[CH3:25]>ClCCl>[CH3:10][C:8]1[O:9][C:5]2[CH:29]=[C:28]([O:27][C:24](=[O:26])[CH3:25])[CH:12]=[CH:11][C:6]=2[CH:7]=1

참가 물질

6

반응물 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 25134Boron tribromideHCID 130130736-Methoxy-2-methylbenzofuran

생성물 1

HCID 221435562-Methylbenzofuran-6-yl acetate수율 82%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A solution of 6-methoxy-2-methyl-benzofuran (17.4 g, 107 mmol) in dichloromethane (200 mL) at 0° C. is treated with boron tribromide (1.0 M, 107 mL). The mixture is stirred at 0° C. for 60 minutes and quenched with water (50 mL). The organic layer is dried over Na2SO4, filtered, and concentrated. The crude product is purified by flash chromatography eluted with 25% EtOAc/Hexanes, and the appropriate fractions are concentrated. The material is dissolved in dichloromethane (150 mL) and triethylamine (17.0 mL, 122 mmol) at 0° C. is treated with acetic acid anhydride (7.22 mL, 76.35 mmol). The reaction is stirred for 16 hours and allowed to warm to room temperature. The reaction is quenched with MeOH (10 mL) and concentrated. The residue is purified by silica gel chromatography with 25% EtOAc/Hexanes to provide acetic acid 2-methyl-benzofuran-6-yl ester (9.50 g, 82%). 1H NMR (400 MHz, CDCl3): δ 7.40-7.38 (d, 1H), 7.15 (s, 1H), 6.91-6.88 (d, 1H), 6.32 (s, 1H), 2.41 (s, 3H), 2.29 (s, 3H).

후처리

  1. customquenched with water (50 mL)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography
  6. washeluted with 25% EtOAc/Hexanes
  7. concentrationthe appropriate fractions are concentrated
  8. dissolutionThe material is dissolved in dichloromethane (150 mL)
  9. stirringThe reaction is stirred for 16 hours
  10. temperatureto warm to room temperature
  11. customThe reaction is quenched with MeOH (10 mL)
  12. concentrationconcentrated
  13. customThe residue is purified by silica gel chromatography with 25% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-516c6f34e68341098316f8785e6487e9
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07846960B2

반응 노트

불러오는 중…