Hydrochloric Acid → 2-(4-Methyl-2-phenyl-1,3-oxazol-5-yl)ethanol

HRID 46026Notes

Reaction equation

HRID 46026 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:17])C.[Li+].[BH4-].Cl>C1COCC1>[CH3:17][C:7]1[N:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:10][C:6]=1[CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 14115754Ethyl(4-methyl-2-phenyl-1,3-oxazol-5-yl)acetate

Product 1

HCID 219427522-(4-Methyl-2-phenyl-1,3-oxazol-5-yl)ethanolYield 25.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl(4-methyl-2-phenyl-1,3-oxazol-5-yl)acetate (0.922 g, 3.76 mmol) in THF (6 mL) at rt, was added LiBH4 2M/THF (9.41 mL, 4.70 mmol). The reaction was stirred overnight at rt, then treated with 2 N HCl until pH 7. The solvent THF was removed under reduced pressure, EtOAc was added, and phases separated. The combined organic extracts were dried over MgSO4 and solvent concentrated in vacuo. The crude material was purified by Biotage using a gradient of 10 to 100% EtOAc/Hexane as solvent mixture. This gave 2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethanol (0.193 g, 25% yield) as colorless oil. ES-MS m/z 204.2 (MH)+); HPLC RT (min.) 2.02; 1H NMR (Acetone-d6) δ 7.98-7.95 (m, 2H), 7.52-7.42 (m, 3H), 3.95 (s br, 1H), 3.82 (t, 2H)m, 2.90 (t, 2H), 2.13 (s, 3H).

Workup

  1. customThe solvent THF was removed under reduced pressure, EtOAc
  2. additionwas added
  3. customphases separated
  4. dry with materialThe combined organic extracts were dried over MgSO4 and solvent
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by Biotage

Sources & evidence

ORD record
ord-bf8336afe9854eacabd174154118a2a4
Source dataset
uspto-grants-2013_09
Patent number
US08541618B2

Reaction notes

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