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

HRID 1007139ノート

反応式

HRID 1007139 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 53401715m-Methoxycinnamyl alcohol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-88f0a62be65e4c31bd9264a2f197b13c
出典データセット
uspto-grants-2004_09
特許番号
US06794384B1

反応ノート

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