Ethyl Acetate → [4-Methyl-2-(1-methyl-cyclohexyl)-oxazol-5-yl]-methanol

HRID 2233282Notes

Reaction equation

HRID 2233282 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[O:16][C:15]([C:17]2([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[N:14][C:13]=1[CH3:24])=O)C.C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[CH3:24][C:13]1[N:14]=[C:15]([C:17]2([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[O:16][C:12]=1[CH2:10][OH:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 59295389HCID 59295389, compound

Product 1

HCID 59295381[4-Methyl-2-(1-methyl-cyclohexyl)-oxazol-5-yl]-methanolYield 92.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.30 g Lithium aluminum hydride was dissolved in 10 ml dry tetrahydrofuran. 2.0 g 4-Methyl-2-(1-methyl-cyclohexyl)-oxazole-5-carboxylic acid ethyl ester, dissolved in 20 ml tetrahydrofuran, were added. The reaction mixture was stirred at room temperature over a period of one hour, then 50 ml ethyl acetate and 50 ml saturated ammonium chloride solution were added to the ice cooled mixture. The reaction mixture was extracted five times with portions of 60 ml of ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure to provide 1.54 g [4-Methyl-2-(1-methyl-cyclohexyl)-oxazol-5-yl]-methanol as an oil.

Workup

  1. additionwere added
  2. temperaturecooled mixture
  3. extractionThe reaction mixture was extracted five times with portions of 60 ml of ethyl acetate
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-22b61c25ccd54767a7625da80fd4d733
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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