Diethyl Ether → HCID 69056857, compound

HRID 860603Notes

Reaction equation

HRID 860603 reaction equation
CON(C)[C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:21])=[O:5].[CH2:23]([Mg]Br)[CH3:24].CCOCC>O1CCCC1.[Cl-].[NH4+]>[CH3:21][C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][CH:16]=2)[O:10][C:6]=1[C:4](=[O:5])[CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 86598133HCID 86598133, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 69056857HCID 69056857, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

4-methyl-2-(4-trifluoromethyl-phenyl)-oxazole-5-carboxylic acid methoxy-methyl-amide (1.0 g, 3.18 mmol) is stirred in tetrahydrofuran (15 mL) at −78° C. ethyl magnesium bromide, 3M/ether (2.1 mL, 4.14 mmol) is added and the mixture is warmed to room temperature. The mixture is diluted with aqueous saturated ammonium chloride and washed with ethyl acetate (three 50 mL portions). The combined ishes are dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue is purified over silica eluting with 7:3 hexanes:ethyl acetate to afford 1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-1-one as an ivory solid, 0.70 g, 78%. MS (M++1) 284.

Workup

  1. additionis added
  2. washwashed with ethyl acetate (three 50 mL portions)
  3. dry with materialThe combined ishes are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified over silica eluting with 7:3 hexanes

Sources & evidence

ORD record
ord-97bbd59eccac47599d0bc69ad36f68fd
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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