Acetic Acid → 3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde oxime

HRID 2428096ノート

反応式

HRID 2428096 の反応式
[C:1]([SiH2:5][O:6][C:7]([CH3:18])([CH3:17])[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH:11]=O)([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].[NH2:24][OH:25].Cl.CC(O)=O>CC#N.CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].O>[C:1]([SiH2:5][O:6][C:7]([CH3:18])([CH3:17])[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH:11]=[N:24][OH:25])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 1373299173-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde

生成物 1

HCID 1373299193-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde oxime収率 112.9%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzaldehyde (12.7 g, 44.6 mmol) was dissolved in CH3CN (53 mL). To this sol. was added NaHCO3 (11.2 g, 134 mmol), and the mixture was stirred vigorously for 5 min. Water (96 mL) was added and the mixture was stirred for 10 min. NH2OH.HCl (6.20 g, 89.2 mmol) was added dropwise, followed by TBAC (622 mg, 2.24 mmol). The mixture was stirred at rt for 1 h, and AcOH (4.00 mL) was added dropwise to pH 6-7. The mixture was diluted with water (100 mL), and this mixture was extracted with Et2O (3×). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (15.1 g, 98%) that was used further without purification. LC-MS: tR=1.09 min; ES+: 341.13.

後処理

  1. stirringthe mixture was stirred for 10 min
  2. stirringThe mixture was stirred at rt for 1 h
  3. extractionthis mixture was extracted with Et2O (3×)
  4. dry with materialextracts were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customDrying the residue under high vacuum

出典と根拠

ORDレコード
ord-b90f016d63f74827a762e76ebeedacb9
出典データセット
uspto-grants-2011_06
特許番号
US07968720B2

反応ノート

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