Imidazole → Ethyl 3-(tributylsilyloxy)picolinate

HRID 986973ノート

反応式

HRID 986973 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 22987980Ethyl 3-(tributylsilyloxy)picolinate収率 49.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5d65a876c250400aa0a6e337bac05068
出典データセット
uspto-grants-2003_10
特許番号
US06630485B2

反応ノート

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