HCID 66815857, compound → HCID 59859851, compound

HRID 1944539Notes

Reaction equation

HRID 1944539 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[CH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12]([CH3:18])([CH3:17])[CH2:11][CH2:10]2)[CH3:2].[H][H]>CO.[Pd]>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[O:13][C:12]([CH3:18])([CH3:17])[CH2:11][CH2:10]2)[CH3:2]

Participants

5

Reactant 2

HCID 66815857HCID 66815857, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59859851HCID 59859851, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-(2,2-Dimethyl-chroman-6-yl)-acrylic acid ethyl ester (1.2 g, 4.61 mmol) in methanol (25 mL) was hydrogenated with 10% palladium on carbon at 60 psi of hydrogen for 6 hours. The catalyst was removed by filtration, and the solvent was evaporated in vacuo to give the product 0.95 g (79%). MS: m/z 263 (MH+). 1H NMR (CDCl3): δ 1.15 (t, 3 H), 1.24 (s, 6 H), 1.70 (t, 2 H), 2.49 (t, 2 H), 2.65 (t, 2 H), 2.76 (t, 2 H), 4.04 (q, 2 H), 6.62 (d, 1 H) and 6.81-6.86 (m, 2 H).

Workup

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

Sources & evidence

ORD record
ord-3ac11528e1c54ffcb71414bbf43abbd3
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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