Propionic Acid → 3-(Quinolin-3-yl)-hex-4-enoic acid ethyl ester

HRID 1837922

반응식

HRID 1837922 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH:11]=[CH:12][CH:13](O)[CH3:14])[CH:2]=1.C(O)(=O)CC.[C:21](OCC)([O:26]CC)([O:23][CH2:24][CH3:25])[CH3:22]>[Cl-].[Na+].O>[CH2:24]([O:23][C:21](=[O:26])[CH2:22][CH:11]([C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:12]=[CH:13][CH3:14])[CH3:25]

참가 물질

5

반응물 3

HCID 1032Propionic AcidHCID 66221Triethyl orthoacetateHCID 542299044-(Quinolin-3-yl)-but-3-en-2-ol

생성물 1

HCID 541558463-(Quinolin-3-yl)-hex-4-enoic acid ethyl ester

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

A solution of the allylic alcohol 22-2 (1.2 g, 6.1 mmol) in triethyl orthoacetate (50 mL) was treated with propionic acid (0.022 mL, 0.31 mmol) and refluxed for 2 h. The cooled mixture was treated with a solution of 1:1 sat. brine/1N HCl (150 mL), then extracted with CH2Cl2 (3×125 mL). The pooled organic extracts were washed with sat. NaHCO3, dried, filtered and evaporated. Chromatography on silica gel (EtOAc) afforded 22-3 as a yellow glass.

후처리

  1. temperaturerefluxed for 2 h
  2. extractionextracted with CH2Cl2 (3×125 mL)
  3. washThe pooled organic extracts were washed with sat. NaHCO3
  4. customdried
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-8bc253619949475d91a0e7848cf74503
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784190B2

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