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

HRID 1454035Notes

Reaction equation

HRID 1454035 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:5][C:6]=1[CH2:7][C:8](OCC)=[O:9].[Li+].[BH4-].Cl>C1COCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:5][C:6]=1[CH2:7][CH2:8][OH:9]

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 8028TetrahydrofuranSolvent

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 2N HCl until pH 7. The solvent THF was removed under reduced pressure, EtOAc was added, and phases separated. The combined organics 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. 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 organics extracts were dried over MgSO4 and solvent
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by Biotage

Sources & evidence

ORD record
ord-8a342a2fc8e244eebea77084ae3bffdb
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

Loading…