Potassium Hydroxide → 5-Methyl-4-pent-4-ynyl-2-phenyl-oxazole

HRID 2121697Notes

Reaction equation

HRID 2121697 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][CH2:15][C:16]#[C:17][Si](C)(C)C.[OH-].[K+]>CO>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH2:15][C:16]#[CH:17]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 120932675-Methyl-2-phenyl-4-(5-trimethylsilanyl-pent-4-ynyl)-oxazole

Product 1

HCID 120932685-Methyl-4-pent-4-ynyl-2-phenyl-oxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Alkyne 1-6 (1.9 g, 6.3 mmol) was dissolved in methanol (100 mL) at 23° C. under N2 atmosphere. An aqueous solution of 10% KOH (10 mL) was then added and the reaction stirred for 12 hours. Solvent removed in vacuo and residue partitioned between ethyl acetate (200 mL) and water (200 mL). The organic layer was washed with water, brine and dried over MgSO4. The crude product 1-7 was used in the following step without further purification.

Workup

  1. customSolvent removed in vacuo and residue
  2. custompartitioned between ethyl acetate (200 mL) and water (200 mL)
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customThe crude product 1-7 was used in the following step without further purification

Sources & evidence

ORD record
ord-e6b2a070d385485b864fb9bca2e12a26
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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