Diethyl Ether → 1-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanol

HRID 860586ノート

反応式

HRID 860586 の反応式
[CH2:1]([C:3]1[N:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:6][C:7]=1[CH:8]=[O:9])[CH3:2].[CH3:20][Mg]Br.C(OCC)C>C1COCC1>[CH2:1]([C:3]1[N:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[O:6][C:7]=1[CH:8]([OH:9])[CH3:20])[CH3:2]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 587657044-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehydeHCID 178418573HCID 178418573、化合物

生成物 1

HCID 587658011-[4-Ethyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-ethyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carbaldehyde (0.793 g, 2.95 mmole) in THF (30 mL) at 0° C., is added a solution of methyl magnesium bromide in diethyl ether (3.0M, 2.0 mL, 0.60 mmole) dropwise. The reaction is stirred for 5 minutes and then warmed up to room temperature for 30 minutes. The reaction is quenched with NH4Cl(aq) (10 mL), partitioned between ethyl acetate (50 mL) and water (50 mL). Extracted the aqueous layer with ethyl acetate (2×50 mL). The combined organic is washed with brine (3×100 mL), dried over Na2SO4, filtered and concentrated to provide the titled compound as a white solid. The crude product is used for the next step without further purification. Mass [EI+] 286 (M+H)+.

後処理

  1. customThe reaction is quenched with NH4Cl(aq) (10 mL)
  2. custompartitioned between ethyl acetate (50 mL) and water (50 mL)
  3. extractionExtracted the aqueous layer with ethyl acetate (2×50 mL)
  4. washThe combined organic is washed with brine (3×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ddcb37fafce74f7d866b5505955fb75c
出典データセット
uspto-grants-2006_12
特許番号
US07153878B2

反応ノート

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