Hydroxyamine hydrochloride → 4-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile

HRID 490393ノート

反応式

HRID 490393 の反応式
Cl.NO.[C:4]([SiH2:8][O:9][C:10]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]1[CH:12]=[C:13]([CH:17]=O)[O:14][C:15]=1[CH3:16])([CH3:7])([CH3:6])[CH3:5].CC1OC=CC=1CCO.[Cl-].ClC1N(C)C=C[N+:43]=1C>ClCCl.O.C(N(CC)CC)C>[C:4]([SiH2:8][O:9][C:10]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:11]1[CH:12]=[C:13]([C:17]#[N:43])[O:14][C:15]=1[CH3:16])([CH3:7])([CH3:6])[CH3:5]

参加物

8

反応物 4

HCID 443297Hydroxyamine hydrochlorideHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chlorideHCID 184446362-(2-Methylfuran-3-yl)ethan-1-olHCID 1317274384-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbaldehyde

生成物 1

HCID 1317274374-(Tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒2 回

実験手順

Hydroxylamine hydrochloride (1.11 g, 16.0 mmoles) and triethylamine (2.22 ml) were added to a solution of 4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbaldehyde from (i)(6.3 g, 16.0 mmoles) in dichloromethane (125 ml) and the mixture was stirred at room temperature for 17 hours. After cooling to 0° C., 2-Chloro-1,3-dimethylimidazolium chloride (2.81 g, 16.6 mmoles) and triethylamine (4.6 ml) were added and the yellow suspension was stirred at room temperature for 24 hours. The mixture was diluted with water and extracted with dichloromethane. The combined extracts were washed with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and water, and finally dried (MgSO4). The solvent was evaporated and the residue was purified by flash chromatography (silica, cyclohexane/diethyl ether 99:1 v/v as eluent) to afford 4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methyl-furan-2-carbonitrile as a viscous oil, (3.75 g).

後処理

  1. temperatureAfter cooling to 0° C.
  2. stirringthe yellow suspension was stirred at room temperature for 24 hours
  3. extractionextracted with dichloromethane
  4. washThe combined extracts were washed with 5% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and water
  5. dry with materialfinally dried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was purified by flash chromatography (silica, cyclohexane/diethyl ether 99:1 v/v as eluent)

出典と根拠

ORDレコード
ord-658a3ba5fb3b4b63926eda0b5bc9e684
出典データセット
uspto-grants-2009_05
特許番号
US07528157B2

反応ノート

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