Methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-fluoromethoxy-acrylate → Methyl 2-(2-hydroxyphenyl)-3-fluoromethoxy-acrylate

HRID 378655Notes

Reaction equation

HRID 378655 reaction equation
O1CCCCC1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[CH:19][O:20][CH2:21][F:22])[C:15]([O:17][CH3:18])=[O:16]>CO>[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=[CH:19][O:20][CH2:21][F:22])[C:15]([O:17][CH3:18])=[O:16]

Participants

3

Reactant 1

HCID 53774316Methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-fluoromethoxy-acrylate

Product 1

HCID 54381247Methyl 2-(2-hydroxyphenyl)-3-fluoromethoxy-acrylateYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.2 g (0.02 mol) of methyl 2-[2-(tetrahydropyran-2-yloxy)-phenyl]-3-fluoromethoxy-acrylate are stirred in 30 ml of methanol at 20° C for 18 hours with 0.5 g of acidic ion exchanger. The ion exchanger is filtered off and the filtrate is concentrated. The residue is chromatographed on silica gel using hexane/acetone (7:3). 3.3 g (73% of theory) of methyl 2-(2-hydroxyphenyl)-3-fluoromethoxy-acrylate are obtained as a pale yellow, viscous oil.

Workup

  1. filtrationThe ion exchanger is filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-8000b48abf674957adf4973d1775b00b
Source dataset
uspto-grants-2000_02
Patent number
US06031107

Reaction notes

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