Trimethylsilyldiazomethane → 3-(5-Methyl-2-phenyl-oxazol-4-yl)-propan-1-ol

HRID 2121694Notes

Reaction equation

HRID 2121694 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15](O)=[O:16].C[Si](C=[N+]=[N-])(C)C.[BH4-].[Na+]>CO.C1(C)C=CC=CC=1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH2:15][OH:16]

Participants

5

Reactant 3

HCID 167693TrimethylsilyldiazomethaneHCID 4311764Sodium borohydrideHCID 120932643-(5-Methyl-2-phenyl-4-oxazolyl)propionic acid

Product 1

HCID 120932653-(5-Methyl-2-phenyl-oxazol-4-yl)-propan-1-olYield 71.3%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

Acid 1-3 (4.6 g, 20 mmol) was dissolved in 300 mL of a 1:1 mixture of methanol/toluene at 23° C. under N2 atmosphere. Trimethylsilyl diazomethane (20 mL, 40 mmol), added dropwise until color persisted and stirred for an additional 4 hours. Solvent was removed in vacuo and residue dried under vacuum for 1 hour. Residue was then redissolved in 300 mL methanol and placed under N2 atmosphere. NaBH4 (10 g, 264 mmol)and the reaction stirred for 4 hours. When complete, solvent was removed in vacuo and residue taken up in ethyl acetate and washed with water, brine and dried over MgSO4. SiO2 chromatography with 40% EtOAc/Hexanes gave 3.1 g of the product 1-4 as white crystals (71%) M.P. NMR CDCl3 (δ): 8.01 (2H, m); 7.44 (3H, m); 3.75 (2H, t, J=5.8, 11.4 Hz); 2.68 (2H, t, 6.8, 13.7 Hz); 2.35 (3H, s); 1.91 (2H, m).

Workup

  1. customSolvent was removed in vacuo and residue
  2. customdried under vacuum for 1 hour
  3. dissolutionResidue was then redissolved in 300 mL methanol
  4. customWhen complete, solvent was removed in vacuo and residue
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-9df11929481b4f5cb5390ac61388f07a
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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