Water → 6-Benzoxazoleethanol, 2-phenyl-

HRID 1023864Notes

Reaction equation

HRID 1023864 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([CH2:16][C:17](OCC)=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[C:14]([CH2:16][CH2:17][OH:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 399486-Benzoxazoleacetic acid, 2-phenyl-, ethyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 30397796-Benzoxazoleethanol, 2-phenyl-Yield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the stirred solution of ethyl 2-(2-phenylbenzo[d]oxazol-6-yl)acetate (Daiichi Pharmaceuticals complay, Ltd, see EP1346982 A1, 2003)(407 mg, 1.37 mmol) in THF (12 mL) was added LAH at 10° C. The reaction mixture was allowed to stir at the same temperature for 2 h, water (0.07 mL), aqueous 15% NaOH (0.07 mL), and water (0.21 mL) were each carefully added to the mixture. The resulting slurry was filtered through a pad of Celite and concentrated in vacuo. The crude product was purified by flash column chromatography to afford the desired product as a clear gel (218 mg, 0.858 mmol, 63%). 1H NMR (DMSO-d6): 2.75 (t, 2H, J=7 Hz), 3.59 (q, 2H, J=7 Hz), 4.62 (t, 1H, J=5.2 Hz), 6.98 (t, 1H, J=7.4 Hz), 7.03 (dd, 1H, J=7.8 Hz, 1.2 Hz), 7.29-7.34 (m, 4H), 7.71 (d, 2H, J=7.6 Hz), 10.51 (s, 1H).

Workup

  1. additioneach carefully added to the mixture
  2. filtrationThe resulting slurry was filtered through a pad of Celite
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-87af63fa7954477a8e4f1429ed3b742a
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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