ethyl {(3aR,5R,6R,6aR)-5-[(E)-2-(4'-chlorobiphenyl-4-yl)vinyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}acetate → ethyl {(3aR,5R,6R,6aR)-5-[2-(4'-chlorobiphenyl-4-yl)ethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}acetate

HRID 84026Notes

Reaction equation

HRID 84026 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C@H:16]3[O:25][C@@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@@H:18]4[C@@H:17]3[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C@H:16]3[O:25][C@@H:19]4[O:20][C:21]([CH3:24])([CH3:23])[O:22][C@@H:18]4[C@@H:17]3[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86700974ethyl {(3aR,5R,6R,6aR)-5-[(E)-2-(4'-chlorobiphenyl-4-yl)vinyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}acetate

Product 1

HCID 86700976ethyl {(3aR,5R,6R,6aR)-5-[2-(4'-chlorobiphenyl-4-yl)ethyl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl}acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound obtained from step g above (0.8 g) in ethyl acetate (15 mL), 10% palladium on charcoal (0.25 g) was added at room temperature. The system was evacuated with hydrogen and the reaction mixture was stirred for 4 hours at room temperature under a hydrogen atmosphere. The reaction mixture was filtered through a celite pad, and concentrated to afford the title compound (0.75 g).

Workup

  1. customThe system was evacuated with hydrogen
  2. filtrationThe reaction mixture was filtered through a celite pad
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2ec5024facb3457886b45348537f30b3
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

Loading…