ethyl 4-(3-benzyloxy-5-fluorophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate → 4-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate Ethyl

HRID 1108066Notes

Reaction equation

HRID 1108066 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:16]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:12]=[C:13]([F:15])[CH:14]=1)C1C=CC=CC=1>[Pd].C(O)C>[F:15][C:13]1[CH:14]=[C:9]([OH:8])[CH:10]=[C:11]([C:16]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[CH:12]=1

Participants

4

Reactant 1

HCID 18786326ethyl 4-(3-benzyloxy-5-fluorophenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate

Product 1

HCID 187863744-(3-Fluoro-5-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate EthylYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-[3-(benzyloxy)-5-fluorophenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxylate (2.70 g, 7.5 mmol) and 10% palladium on activated carbon (0.27 g) in ethanol (100 ml) was stirred under a hydrogen atmosphere for 3.25 hr. Catalyst was removed by filtration and evaporation of the filtrate gave the titled compound as a colorless liquid (2.01 g, quantitative yield).

Workup

  1. customCatalyst was removed by filtration and evaporation of the filtrate

Sources & evidence

ORD record
ord-435b58389b02449a8ff1bd6a62f1fa96
Source dataset
uspto-grants-2000_05
Patent number
US06063928

Reaction notes

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