HCID 89581294, compound → HCID 89580553, compound

HRID 1501170Notes

Reaction equation

HRID 1501170 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:8][CH:7]=1>CO.[Pd]>[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]1[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 89581294HCID 89581294, compound

Product 1

HCID 89580553HCID 89580553, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(furan-2-yl)benzoate (400 mg, 1.64 mmol) in methanol (20 mL) was added palladium on carbon (10%, 100 mg). After stirring for 24 hours at room temperature under hydrogen atmosphere, the mixture was filtered. And the filtrate was concentrated in vacuo to give tert-butyl 4-(tetrahydrofuran-2-yl)benzoate (350 mg, 86%) as a white solid. LRMS (M+H+) m/z: calcd 248.14. found 248. 1H NMR (300 MHz, CD3OD): δ 7.94-7.85 (m, 2H), 7.44-7.28 (m, 2H), 4.95-4.93 (m, 1H), 3.60-3.56 (m, 2H), 2.73-2.68 (m, 2H), 1.77-1.73 (m, 2H), 1.68 (s, 9H).

Workup

  1. filtrationthe mixture was filtered
  2. concentrationAnd the filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-5853d2e6105c42ff9c71d40ba4770e76
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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