Potassium Hydroxide → (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester

HRID 885893노트

반응식

HRID 885893 반응식
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:11])[CH3:10])=[CH:5][CH:4]=1.[C:12]([O:16][C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][N:21]=1)([CH3:15])([CH3:14])[CH3:13].[OH-].[K+]>CCO>[C:12]([O:16][C:17](=[O:28])/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:10]/[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[O:11])=[CH:22][N:21]=1)([CH3:15])([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 5852641-(4-(Hydroxymethyl)phenyl)ethanoneHCID 44819897tert-Butyl (E)-3-(5-formyl-pyridin-2-yl)-acrylate

생성물 1

HCID 67049926(E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester수율 34.5%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
0 °C

실험 절차

A solution of 1-(4-hydroxymethyl-phenyl)-ethanone (750 mg, 5 mmol) in EtOH (15 ml) was added dropwise at 0° C. to a stirred solution of (E)-3-(5-formyl-pyridin-2-yl)-acrylic acid tert-butyl ester (described in Example 11 STEP A-D, 1.16 g, 5 mmol) and 1.7 M KOH (4.4 ml) in EtOH (10 ml). The mixture was stirred at 0° C. for 5 h and the resulting precipitate was filtered and triturated with di-isopropylether to give 630 mg of desired (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester. The mother liquors were diluted with water and extracted with AcOEt. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was triturated with EtOH to give additional 70 mg of (E)-3-{5-[(E)-3-(4-hydroxymethyl-phenyl)-3-oxo-propenyl]-pyridin-2-yl}-acrylic acid tert-butyl ester.

후처리

  1. filtrationthe resulting precipitate was filtered
  2. customtriturated with di-isopropylether

출처 및 근거

ORD 기록
ord-affe6ed0ebbf401793d5aac7c4011cce
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242175B2

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