Imidazole → Ethyl 3-(tributylsilyloxy)picolinate

HRID 1017666

반응식

HRID 1017666 반응식
[OH:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:13]([Si:17](Cl)([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:15][CH3:16].N1C=CN=C1.O>C(Cl)Cl>[CH2:22]([Si:17]([CH2:13][CH2:14][CH2:15][CH3:16])([CH2:18][CH2:19][CH2:20][CH3:21])[O:1][C:2]1[C:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1)[CH2:23][CH2:24][CH3:25]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 70448TributylchlorosilaneHCID 15080989Ethyl 3-hydroxypicolinate

생성물 1

HCID 22987980Ethyl 3-(tributylsilyloxy)picolinate수율 49.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of ethyl 3-hydroxypicolinate (15 g, 900 mmol), tributylsilyl chloride (16.23 g, 110 mmol), imidazole (8.0 g, 120 mmol) in methylene chloride was stirred overnight under a nitrogen atmosphere. Water was added and the methylene chloride layer was separated and concentrated in vacuo. Purification on a silica gel column using ethyl acetate-hexane (1:4) as the eluant gave ethyl 3-(tributylsilyloxy)picolinate as a solid (20 g).

후처리

  1. customthe methylene chloride layer was separated
  2. concentrationconcentrated in vacuo
  3. customPurification on a silica gel column

출처 및 근거

ORD 기록
ord-99c87da307f14c518c593c22d41da186
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479507B2

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