Aluminium lithium hydride → [2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-yl]-methanol

HRID 2233566Notes

Reaction equation

HRID 2233566 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[O:9][C:10]=1[CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:26][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:8]2[O:9][C:10]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)=[C:6]([CH2:4][OH:3])[N:7]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 592961772-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazole-4-carboxylic acid ethyl ester

Product 1

HCID 59296161[2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-yl]-methanolYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.3 g 2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazole-4-carboxylic acid ethyl ester were dissolved in 100 ml tetrahydrofuran and cooled in an ice bath. 21.8 ml of a one molar solution of lithium aluminium hydride in tetrahydrofuran were added. The cooling bath was removed and the reaction mixture stirred at room temperature for thirty minutes. The reaction mixture was cooled in an ice bath again and sequentially added 6 ml water, 12 ml 15% NaOH and 18 ml water. After being stirred for one hour at room temperature the reaction mixture was filtered over a pad of celite and washed with ethyl acetate. The filtrate was dried over MgSO4 and the solvent was removed in vacuo and the residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=6:4=>9:1=>ethyl acetate) to obtain 3.0 g [2-(4-Methoxy-phenyl)-5-(tetrahydro-pyran-2-yloxymethyl)-oxazol-4-yl]-methanol.

Workup

  1. temperaturecooled in an ice bath
  2. customThe cooling bath was removed
  3. temperatureThe reaction mixture was cooled in an ice bath again
  4. stirringAfter being stirred for one hour at room temperature the reaction mixture
  5. filtrationwas filtered over a pad of celite
  6. washwashed with ethyl acetate
  7. dry with materialThe filtrate was dried over MgSO4
  8. customthe solvent was removed in vacuo
  9. customthe residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=6:4=>9:1=>ethyl acetate)

Sources & evidence

ORD record
ord-572da2ceb3134e9da83e6d9e3f5e6bdb
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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