Benzyl Alcohol → HCID 54453405, compound

HRID 986479Notes

Reaction equation

HRID 986479 reaction equation
COC(=O)CC1N=C(N[C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=O)SC=1.[CH2:22]([OH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:30][O-:31].[Na+].[CH3:33]O>C1(C)C=CC=CC=1>[CH2:22]([O:29][C:30](=[O:31])[CH:33]=[CH:11][O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 887MethanolHCID 10942334Sodium MethoxideHCID 14121877Methyl (2-{[(benzyloxy)carbonyl]amino}-1,3-thiazol-4-yl)acetate

Product 1

HCID 54453405HCID 54453405, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-methoxyacrylic acid methyl ester (1), benzyl alcohol (1.2 equivalents), a solution of sodium methoxide in methanol (0.05 equivalents), and toluene (3.7 parts) is heated for 3 hours to remove methanol under azeotropic distillation. The mixture is concentrated in vacuo to remove the solvent, distilled in vacuo to remove by-products (94° to 112° C. at 3 mmHg), and cooled. The residue is chromatographed over silica gel (benzene:ethyl acetate=95:5) to give 3-benzyloxyacrylic acid benzyl ester (2). Yield: 45%.

Workup

  1. customto remove methanol
  2. distillationunder azeotropic distillation
  3. concentrationThe mixture is concentrated in vacuo
  4. customto remove the solvent
  5. distillationdistilled in vacuo
  6. customto remove by-products (94° to 112° C. at 3 mmHg)
  7. temperaturecooled
  8. customThe residue is chromatographed over silica gel (benzene:ethyl acetate=95:5)

Sources & evidence

ORD record
ord-250a01967f824635a70b086f40012719
Source dataset
uspto-grants-1987_12
Patent number
US04713461

Reaction notes

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