Methyl Vanillate → HCID 58550981, compound

HRID 2204161Notes

Reaction equation

HRID 2204161 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:14][CH3:15].FC(F)(F)S(O[CH2:22][CH2:23][O:24][C:25]([F:28])([F:27])[F:26])(=O)=O>CN(C=O)C>[CH3:15][O:14][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=1[O:3][CH2:22][CH2:23][O:24][C:25]([F:28])([F:27])[F:26])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 19844Methyl VanillateHCID 24758Sodium hydrideHCID 106351812-(Trifluoromethoxy)ethyl trifluoromethanesulfonate

Product 1

HCID 58550981HCID 58550981, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium hydride (200 mg, 5.0 mmol) in DMF (6 mL) under N2 was added methyl 4-hydroxy-3-methoxy-benzoate (920 mg, 5.0 mmol) and the mixture was stirred for 10 min. 2-(Trifluoromethoxy)ethyl trifluoromethanesulfonate (prepared according to the procedure described by Blazejewski, et. al. JOC, 2001, 66(3), 1061-1063) (1.2 g, 4.6 mmol) was then added dropwise and the solution was stirred at room temperature for 2 h, then at 50° C. for 2 h. The mixture was concentrated to a solid, and the residue was taken up in 50 mL of DCM before it was washed with brine (20 mL), dried over MgSO4 and purified by column chromatography (0-25% EtOAc/hexane) to give methyl 3-methoxy-4-(2-(trifluoromethoxy)ethoxy)benzoate as a white solid. ESI-MS m/z calc. 294.1, found 295.3 (M+1)+; Retention time: 1.63 minutes (3 min run).

Workup

  1. additionwas then added dropwise
  2. stirringthe solution was stirred at room temperature for 2 h
  3. waitat 50° C. for 2 h
  4. concentrationThe mixture was concentrated to a solid
  5. washwas washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. custompurified by column chromatography (0-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-bd86b40738734a29b026a76d510c5d8f
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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