HCID 89580620, compound → HCID 89580621, compound

HRID 1500955Notes

Reaction equation

HRID 1500955 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:8][CH:7]=2)=[CH:2]1>CO.[Pd]>[O:1]1[CH2:5][CH2:4][CH:3]([C:6]2[CH:18]=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[CH:8][CH:7]=2)[CH2:2]1

Participants

4

Reactant 1

HCID 89580620HCID 89580620, compound

Product 1

HCID 89580621HCID 89580621, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(furan-3-yl)benzoate (400 mg, 1.64 mmol) in methanol (20 mL) was added palladium on carbon (10%, 40 mg), and the mixture was stirred for 24 hours at room temperature under hydrogen atmosphere. Insoluble matters were removed using celite, and the filtrate was concentrated in vacuum to give title product as a white solid (350 mg, 86%). LRMS (M+H+) m/z: calcd 248.14. found 248 1H NMR (300 MHz, CD3OD): δ 7.91 (m, 2H), 7.38 (d, J=8.4 Hz, 2H), 4.09 (m, 2H), 3.95 (m, 1H), 3.87 (m, 1H), 3.72 (m, 1H), 2.45 (m, 1H), 2.36 (m, 1H), 1.59 (s, 9H).

Workup

  1. customInsoluble matters were removed
  2. concentrationthe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-dda74ab2517545739473031f80fd0b81
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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