Diethyl Ether → HCID 69056857, compound

HRID 490726Notes

Reaction equation

HRID 490726 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 washes 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. washwashed with ethyl acetate (three 50 mL portions)
  2. dry with materialThe combined washes are dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified over silica eluting with 7:3 hexanes

Sources & evidence

ORD record
ord-5d83fec4b2b84a72bcec68376429f9fc
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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