HCID 10441877, compound → Methyl 3-(furan-3-yl)propanoate

HRID 1585453Notes

Reaction equation

HRID 1585453 reaction equation
[O:1]1[CH:5]=[CH:4][C:3](/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])=[CH:2]1>C1COCC1.[Pd]>[O:1]1[CH:5]=[CH:4][C:3]([CH2:6][CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:2]1

Participants

4

Reactant 1

HCID 10441877HCID 10441877, compound

Product 1

HCID 18470351Methyl 3-(furan-3-yl)propanoateYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11a (2.0 g, 13.15 mmol) in 45 mL dry THF was treated with 10% Pd-C (30.0 mg, 1.5 wt %) at room temperature under a hydrogen atmosphere (balloon) (44 h). The reaction mixture was then filtered through a Celite plug, washed with EtOAc (150 mL), and concentrated in vacuo. SGC chromatotron (SiO2, 4 mm, 10-20% EtOAc/hexanes) afforded 12a (1.89 g, 2.03 g theoretical, 93%). For 12a: 1H NMR (CDCl3, 250 MHz) d 7.29 (br d, 1H, J=1.6 Hz, Fur C5-H), 7.19 (d, 1H, J=1.6 Hz, Fur C2-H), 6.22 (br s, 1H, Fur C4-H), 3.63 (s, 3H, OCH3), 2.71 (t, 2H, J=7.3 Hz, FurCH2), 2.52 (t, 2H, J=7.3 Hz, CH2 (C=O)); 13C NMR (CDCl3, 125 MHz) d 173.2, 142.8, 138.9, 123.4, 110.6, 51.5, 34.4, 20.1; IR (neat) nmax 2932, 2862, 1732, 1439, 1361, 1259, 1201, 1167, 1024, 874, 793, 731 cm-1. See FIG. 17h.

Workup

  1. filtrationThe reaction mixture was then filtered through a Celite plug
  2. washwashed with EtOAc (150 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6b4d21d3120a48439c2d176c12ac22ad
Source dataset
uspto-grants-1999_08
Patent number
US05939268

Reaction notes

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