Chlorotrimethylsilane → HCID 22323650、化合物

HRID 495876ノート

反応式

HRID 495876 の反応式
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][OH:8].C[Si](Cl)(C)C.[C:14]1([C:20]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:21]Cl)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.C(Cl)Cl>[OH:1][CH2:2][CH2:3][N:4]([S:21][C:20]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:5][CH2:6][CH2:7][OH:8]

参加物

6

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 342378Triphenylmethanesulfenyl ChlorideHCID 30150593-((2-Hydroxyethyl)amino)propanol

生成物 1

HCID 22323650HCID 22323650、化合物

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

N-(2-hydroxyethyl)-3-amino-1-propanol (5.0 g, 41.9 mmol) is coevaporated several times with pyridine (20 mL) and then dissolved in pyridine (100 mL). The reaction flask is flushed with Argon and trimethylsilylchloride (2.47 g, 209.5 mmol) is added dropwise. The reaction mixture is stirred for 1 hour. Triphenyl methanesulfenyl chloride (14.32 g, 46.09 mmol) is dissolved in CH2Cl2 and added via dropping funnel to the cooled reaction mixture. The reaction mixture is warmed to room temperature and stirred for 18 hours. The reaction mixture is concentrated in vacuo and the resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1). The H2O layer is separated and extracted with EtOAc (3×50 ml). The EtOAc extracts are pooled, dried (MgSO4) and filtered. The filtrate is concentrated in vacuo and the residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent. The appropriate fractions are pooled and concentrated in vacuo to give the title compound.

後処理

  1. additionis added dropwise
  2. additionadded
  3. customto the cooled reaction mixture
  4. stirringstirred for 18 hours
  5. concentrationThe reaction mixture is concentrated in vacuo
  6. customthe resultant residue is partitioned between H2O and EtOAc (100 ml, 1:1)
  7. customThe H2O layer is separated
  8. extractionextracted with EtOAc (3×50 ml)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationThe filtrate is concentrated in vacuo
  12. customthe residue is purified by silica gel flash column chromatography with EtOAc/hexanes as the eluent
  13. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cf8487b5e33d45c7bec7cbeef436f326
出典データセット
uspto-grants-2005_09
特許番号
US06942966B1

反応ノート

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