Aluminium lithium hydride → HCID 59296152, compound

HRID 2263388Notes

Reaction equation

HRID 2263388 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[O:16][C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:14][C:13]=1[CH2:25][O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)=O)C>O1CCCC1>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[O:16][C:12]([CH2:10][OH:9])=[C:13]([CH2:25][O:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][O:28]3)[N:14]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59296143HCID 59296143, compound

Product 1

HCID 59296152HCID 59296152, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled suspension of 2.73 g lithium aluminium hydride in 180 ml tetrahydrofuran a solution of 12.3 g 2-(4-methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazole-5-carboxylic acid ethyl ester in 120 ml tetrahydrofuran were added at 0° C. The ice bath was removed and the reaction mixture stirred at room temperature for one hour. The reaction mixture was cooled in an ice bath again and 100 ml ethyl acetate were added followed by the addition of 300 ml methyl-tert-butyl ether. Then a solution of 10.92 g sodium hydroxide in 12.3 ml water was added. Solid precipitate was filtered off through a plug of celite. The filtrate was dried over MgSO4 and then the solvent was removed in vacuo to obtain 11.8 g [2-(4-methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazol-5-yl]-methanol as a solid.

Workup

  1. additionwere added at 0° C
  2. customThe ice bath was removed
  3. temperatureThe reaction mixture was cooled in an ice bath again
  4. addition100 ml ethyl acetate were added
  5. additionfollowed by the addition of 300 ml methyl-tert-butyl ether
  6. additionThen a solution of 10.92 g sodium hydroxide in 12.3 ml water was added
  7. filtrationSolid precipitate was filtered off through a plug of celite
  8. dry with materialThe filtrate was dried over MgSO4
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-aaade92cb7a447abba839b6e14209a7f
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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