2-Propenoic acid, 3-(3-methoxyphenyl)- → m-Methoxycinnamyl alcohol

HRID 1007139노트

반응식

HRID 1007139 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[CH:12]=[CH:13][C:14](O)=[O:15].[K+].[Br-]>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[CH:12]=[CH:13][CH2:14][OH:15]

참가 물질

5

반응물 3

HCID 871552-Propenoic acid, 3-(3-methoxyphenyl)-HCID 253877Potassium BromideHCID 21226445Aluminium lithium hydride

생성물 1

HCID 53401715m-Methoxycinnamyl alcohol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

Lithium aluminium hydride (213 mg; 5.5 mmol) was added portionwise to anhydrous THF (10 ml) at 0° C. To this a solution of 3-methoxycinnamic acid (2 g; 11 mmol) in THF (5 ml) was added. The reaction was left to stir at 0° C. for 10 min and then allowed to reach ambient temperature. The reaction mixture was quenched with 2M aqueous sodium hydroxide (15 ml) and the aqueous layer was extracted with ether (3×15 ml). The combined organic layers were washed with 2M hydrochloric acid (3×15 ml), brine (3×15 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel, and the product was isolated as an oil (222 mg: 12%). IR (cm−1; KBr): (3400, OH) (1400; C═C) (1250; OCH3); 1H-NMR CDCl3: (3.8, s; 3H) (4.3, dd; 2H) (6.3, m; 1H) (6.6, d; 1H) (6.8, dd; 1H) (6.9, t; 1H) (7.0, d; 1H) (7.2, t: 1H); 13C-NMR CDCl3: 55.3, 63.6, 111.9, 113.4, 119.2, 128.9, 129.6, 131.0, 138.2, 158.2, 159.9; Mass Spectrum (M+) m/e: 164.

후처리

  1. waitThe reaction was left
  2. customto reach ambient temperature
  3. customThe reaction mixture was quenched with 2M aqueous sodium hydroxide (15 ml)
  4. extractionthe aqueous layer was extracted with ether (3×15 ml)
  5. washThe combined organic layers were washed with 2M hydrochloric acid (3×15 ml), brine (3×15 ml)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel
  9. customthe product was isolated as an oil (222 mg: 12%)

출처 및 근거

ORD 기록
ord-88f0a62be65e4c31bd9264a2f197b13c
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794384B1

반응 노트

불러오는 중…