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

HRID 362874노트

반응식

HRID 362874 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 232935663-(4-Fluorophenyl)pentanoic acid수율 83.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-e0caafa1973f487289cdb9a5cdafe8b5
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05872118

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