3-[Hydroxy(3-methoxyphenyl)methyl)-2-oxotetrahydrofuran → 3-(3-Methoxybenzyl)-2-oxotetrahydrofuran

HRID 1741354Notes

Reaction equation

HRID 1741354 reaction equation
O[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[CH:3]1[CH2:7][CH2:6][O:5][C:4]1=[O:8]>C(O)C.[Pd]>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[CH2:2][CH:3]1[CH2:7][CH2:6][O:5][C:4]1=[O:8]

Participants

4

Reactant 1

HCID 183672943-[Hydroxy(3-methoxyphenyl)methyl)-2-oxotetrahydrofuran

Product 1

HCID 183673643-(3-Methoxybenzyl)-2-oxotetrahydrofuranYield 86.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-[hydroxy(3-methoxyphenyl)methyl]-2-oxotetrahydrofuran (1.0 g) and 10% Pd/C (0.5 g) in ethanol (20 ml) was stirred under H2 for 10 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo to give 3-(3-methoxybenzyl)-2-oxotetrahydrofuran (0.8 g) MS (m/z): 207 (M+ +1) IR (Neat): 1750 cm-1NMR (CDCl3, δ): 2.0-2.6 (4H, m), 2.7-3.2 (3H, m), 3.79 (3H, s), 4.1-4.4 (2H, m), 6.7-7.1 (3H, m), 7.2-7.4 (1H, m)

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-ce696be502c8435a8097672bd62e6cf1
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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