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

HRID 1715398노트

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HRID 1715398 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 962Water용매2회HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b74387f8727d4468881099a4baad25f8
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799805B2

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