Acetic Acid → HCID 59295378, compound

HRID 2233291Notes

Reaction equation

HRID 2233291 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2(Br)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:8][C:7]=1[CH2:18]Br)=[O:5])C.C[O-].[Na+].[C:23](O)(=[O:25])C>CO>[CH3:1][O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)=[N:8][C:7]=1[CH2:18][O:25][CH3:23])=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 59295387HCID 59295387, compound

Product 1

HCID 59295378HCID 59295378, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

14.7 g 2-(1-Bromo-cyclohexyl)-4-bromomethyl-oxazole-5-carboxylic acid ethyl ester were dissolved in 150 ml methanol. 6.03 g sodium methylate were added and the reaction mixture stirred at 65° C. for one hour. The cooled reaction mixture was acidified by addition of acetic acid (pH˜6). The solvent was removed in vacuo. The residue was dissolved in 250 ml ethyl acetate and washed with 80 ml water and brine, dried over MgSO4 and then the solvent was removed in vacuo. The residue was purified by reversed phase HPLC to obtain 5.30 g 2-Cyclohex-1-enyl-4-methoxymethyl-oxazole-5-carboxylic acid methyl ester as an oil.

Workup

  1. customThe cooled reaction mixture
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in 250 ml ethyl acetate
  4. washwashed with 80 ml water and brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-01e482362af046aca5f00553241b2704
Source dataset
uspto-grants-2010_05
Patent number
US07709481B2

Reaction notes

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