HCID 86759970, compound → HCID 22184672, compound

HRID 1795067Notes

Reaction equation

HRID 1795067 reaction equation
[CH:1]([Si:4]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][C:10](=[CH:13][C:14]([O:16][CH3:17])=[O:15])[CH2:9][CH2:8]1)([CH3:3])[CH3:2]>[Pd].CO>[CH:21]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:18]([CH3:20])[CH3:19])[O:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]([CH2:13][C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:12]1)([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 86759970HCID 86759970, compound

Product 1

HCID 22184672HCID 22184672, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10.3 g (30.2 mmol) of the unsaturated ester from Step D and 600 mg of 5% palladium on carbon in 150 mL of methanol was stiffed under an atmosphere of hydrogen for 3 h. The catalyst was filtered off and the filtrate concentrated to give 8.8 g (85%) of the title compound as a mixture of cis and trans isomers. 1H NMR (500 MHz, CDCl3) δ 3.68 (s, 3H), 3.57 (d, 0.6H, J=6.7 Hz), 3.39 (d, 1.4H, J=6.2 Hz), 2.32 (d, 0.6H, J=4.4 Hz), 2.21 (d, 1.4H, J=3.9 Hz), 1.82–1.60 (m, 4H), 1.54 (m, 1H), 1.45 (m, 1H), 1.1–1.05 (m, 21H), 1.01 (m, 2H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-56eed9af25864eb89a84afdc41ccb45a
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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