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

HRID 1397434ノート

反応式

HRID 1397434 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 65367Trimethylsilyl triflate触媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-308ab216c17e4a37977342d644cea64f
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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