Potassium Hydroxide → 3-(4-Fluorophenyl)pentanoic acid

HRID 362874ノート

反応式

HRID 362874 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:15][CH3:16])[CH2:9][C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[K+]>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:15][CH3:16])[CH2:9][C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 23293610Ethyl 3-(4-fluorophenyl)valerate

生成物 1

HCID 232935663-(4-Fluorophenyl)pentanoic acid収率 83.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

This compound was prepared in an analogous manner to Example 18c with the replacement of 3-(4-fluorophenyl)butyrate with ethyl 3-(4-fluorophenyl)valerate (38.95 g 0.144 mol, containing 29% triethyl phosphoneacetate) and using an excess of 85% potassium hydroxide (18.05 g, 0.273 mol, Mallinckrodt). The dichloromethane layers were combined, washed with deionized water (50 ml) and concentrated by spin evaporation in vacuo. The residue was crystallized from hexanes to give 23.47 g (83%) of 3-(4-flurophenyl)valeric acid as a white crystalline solid: NMR (DMSO-d6): d 12 (s, 1H), 7.28-7.24 (m, 2H), 7.14-7.08 (m, 2H), 2.91-2.89 (m, 1H), 2.64-2.41 (m, 2H), 1.66-162 (m, 1H), 1.56-1.51 (m, 1H), 0.71 (t, 3H, J=7.3 Hz).

後処理

  1. washwashed with deionized water (50 ml)
  2. concentrationconcentrated by spin evaporation in vacuo
  3. customThe residue was crystallized from hexanes

出典と根拠

ORDレコード
ord-e0caafa1973f487289cdb9a5cdafe8b5
出典データセット
uspto-grants-1999_02
特許番号
US05872118

反応ノート

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