2,4,5-Trifluorophenylacetic acid → 2-(2,4,5-Trifluorophenyl)ethan-1-ol

HRID 718358

反応式

HRID 718358 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11](O)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][CH2:11][OH:12]

参加物

4

反応物 2

HCID 27779502,4,5-Trifluorophenylacetic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 177508392-(2,4,5-Trifluorophenyl)ethan-1-ol収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-(2,4,5-trifluorophenyl)acetic acid (1 g, 5.26 mmol) in dry THF (20 mL) was carefully added over 2 min to solution of 2M LAH (10.52 mL, 10.52 mmol) at 0° C. The reaction mixture was allowed to warm to rt and was stirred for 6 h. The reaction was quenched with 0.5 mL of water (stir for 10 min), 0.5 mL of 15% NaOH/water (stir for 10 min), and then 1.0 mL of water. After stirring for 18 h, the mixture was filtered through celite. The filtrate was concentrated in vacuum. The residue was dried under high vacuum for 16 h to afford 2-(2,4,5-trifluorophenyl)ethanol (850 mg, 4.83 mmol, 92% yield) as a clear viscous oil, which was used as is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.11 (ddd, J=10.3, 8.7, 7.2 Hz, 1H), 6.93 (td, J=9.7, 6.6 Hz, 1H), 3.87 (t, J=6.5 Hz, 2H), 2.88 (t, J=6.5 Hz, 2H).

後処理

  1. customThe reaction was quenched with 0.5 mL of water (stir for 10 min), 0.5 mL of 15% NaOH/water (stir for 10 min)
  2. stirringAfter stirring for 18 h
  3. filtrationthe mixture was filtered through celite
  4. concentrationThe filtrate was concentrated in vacuum
  5. customThe residue was dried under high vacuum for 16 h

出典と根拠

ORDレコード
ord-f0a353c24d1b4510a32efe4af3ee6e52
出典データセット
uspto-grants-2015_11
特許番号
US09193720B2

関連ノート

読み込み中…