Dichloromethane → 4-(Dimethoxymethyl)-2-(4-fluorophenyl)oxazole

HRID 1397434노트

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HRID 1397434 반응식
[CH3:1][O:2][Si](C)(C)C.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][CH:16]=[C:17]([CH:19]=[O:20])[N:18]=2)=[CH:10][CH:9]=1.[CH2:21](Cl)Cl>FC(F)(F)S(O[Si](C)(C)C)(=O)=O>[CH3:21][O:20][CH:19]([O:2][CH3:1])[C:17]1[N:18]=[C:14]([C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=2)[O:15][CH:16]=1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 15771MethoxytrimethylsilaneHCID 218062352-(4-Fluoro-phenyl)-oxazole-4-carbaldehyde

생성물 1

HCID 673246204-(Dimethoxymethyl)-2-(4-fluorophenyl)oxazole

시약·촉매·용매 1

HCID 65367Trimethylsilyl triflate촉매

실험 절차

Methoxytrimethylsilane (545 mg, 5.23 mmol) and trimethylsilyl trifluoromethanesulfonate (30 mg, 0.13 mmol) were added to a solution of 2-(4-fluorophenyl)oxazole-4-carbaldehyde (500 mg, 2.62 mmol) in dry CH2Cl2 (2 mL) at −78° C. The reaction mixture was allowed to warm up to room temperature and stirred for 24 h, quenched with saturated aqueous NaHCO3 solution, and the crude product was extracted with EtOAc. The organic layer was washed with 10% NaHCO3 solution, water and brine and dried over anhydrous sodium sulfate. Solvent was removed under reduced pressure to get 4-(dimethoxymethyl)-2-(4-fluorophenyl)oxazole (400 mg, crude), which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 8.08-8.05 (m, 2H), 7.71 (d, J=1.2 Hz, 1H), 7.16-7.12 (m, 2H), 5.50 (d, J=0.9 Hz, 1H), 3.41 (s, 6H). MS (ESI) m/z: Calculated for C12H12FNO3: 237.08. found: 259.9 (M+Na)+.

후처리

  1. customquenched with saturated aqueous NaHCO3 solution
  2. extractionthe crude product was extracted with EtOAc
  3. washThe organic layer was washed with 10% NaHCO3 solution, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-308ab216c17e4a37977342d644cea64f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

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