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Hydrochloric Acid → 5-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-3-oxo-pentanenitrile

HRID 2285272
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HRID 2285272 반응식
[H-].[Na+].C[O:4][C:5](=O)[C:6]([CH3:27])([CH3:26])[CH2:7][O:8][Si:9]([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:29](#[N:31])[CH3:30].Cl>C1(C)C=CC=CC=1>[C:22]([Si:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:8][CH2:7][C:6]([CH3:27])([CH3:26])[C:5](=[O:4])[CH2:30][C:29]#[N:31])([CH3:25])([CH3:23])[CH3:24]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 16067138Methyl 3-((tert-butyldiphenylsilyl)oxy)-2,2-dimethylpropanoate

생성물 1

HCID 866872835-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-3-oxo-pentanenitrile수율 25%

시약·촉매·용매 1

HCID 1140
Toluene
용매
2회

실험 절차

A suspension of sodium hydride (60% dispersion in oil) (2.12 g, 52.9 mmol) in toluene (65 mL) at reflux under N2 was added over 55 mins a solution of Intermediate 153a (15.93 g, assumed 37.8 mmol) and acetonitrile (2.87 mL, 54.9 mmol) in toluene (31 mL). The mixture was heated at reflux for 67 h. The cooled reaction mixture was slowly acidified to pH 5 with aqueous 1N HCl and extracted with EtOAc. The aqueous layer was extracted with EtOAc (×2) and the combined organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by FCC, using 0-50% ether in pentane, to give the title compound (3.52 g, 25%) as a yellow oil. LCMS (Method 3): Rt 4.94 min, m/z 402.3 [M+Na+].

후처리

  1. temperatureat reflux under N2
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 67 h
  4. customThe cooled reaction mixture
  5. extractionextracted with EtOAc
  6. extractionThe aqueous layer was extracted with EtOAc (×2)
  7. washthe combined organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by FCC

출처 및 근거

ORD 기록
ord-c85540d5838f4791bcf31cb5409fe7ce
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145413B2

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