HCID 7269394, compound → Ethyl 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate

HRID 1361912Notes

Reaction equation

HRID 1361912 reaction equation
[CH3:1][C:2]1([CH3:14])[O:6][C@H:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][O:3]1>[Pd].CO>[CH3:1][C:2]1([CH3:14])[O:6][C@H:5]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][O:3]1

Participants

4

Reactant 1

HCID 7269394HCID 7269394, compound

Product 1

HCID 22831642Ethyl 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a methanol (200 mL) solution of ethyl (2E)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate (15.3 g, 76.7 mmol) was added 10% palladium on carbon (1.5 g). The reaction mixture was stirred under an atmosphere of hydrogen overnight. The catalyst was removed by filtration, and the solvent was removed in vacuo. Chromatography over silica afforded the title compound. 1H NMR (400 MHz, CDCl3): δ 4.05-4.15 (m, 2H), 4.02-4.04 (m, 2H), 3.52-3.55 (m, 1H), 2.30-2.47 (m, 2H), 1.83-1.90 (m, 2H), 1.33 (s, 3H), 1.26 (s, 3H), 1.21 (t, J=6.8 Hz, 3H).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-abb701668b8f438ea180783a7c4649c6
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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