Tetrahydrofuran → HCID 58765814, compound

HRID 860604Notes

Reaction equation

HRID 860604 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[O:5][C:6]=1[C:7](=[O:10])[CH2:8][CH3:9].O1CCCC1.[BH4-].[Li+]>Cl>[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=2)[O:5][C:6]=1[CH:7]([OH:10])[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 69056857HCID 69056857, compound

Product 1

HCID 58765814HCID 58765814, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-1-one (0.68 g, 2.4 mmol) and tetrahydrofuran (5 mL) are stirred at 0° C. Lithium borohydride (0.14 g, 6.36 mmol) is added and the mixture is stirred 10 min at 0° C., and 30 min at room temperature. The mixture is diluted with 1M aqueous hydrochloric acid and washed with ethyl acetate (three 50 mL portions). The organic ishes are dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is purified over silica eluting with 8:2 hexanes:ethyl acetate to 1:1 hexanes ethyl acetate to afford 1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propan-1-ol as ivory solid, 0.69 g, 100%. MS (M++1) 286.

Workup

  1. custom30 min
  2. customat room temperature
  3. washwashed with ethyl acetate (three 50 mL portions)
  4. dry with materialThe organic ishes are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified over silica eluting with 8:2 hexanes

Sources & evidence

ORD record
ord-c4af197b18b044be9421ac65c5a3fcbb
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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