HCID 69031670, compound → HCID 69031120, compound

HRID 750473Notes

Reaction equation

HRID 750473 reaction equation
[CH3:1][C:2]1([CH3:34])[O:6][C@H:5]([C@@:7]([OH:31])([CH:29]=C)[CH2:8][O:9][C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:4]([CH:32]=C)[O:3]1>C(Cl)Cl>[CH3:34][C:2]1([CH3:1])[O:3][C@H:4]2[CH:32]=[CH:29][C@:7]([CH2:8][O:9][C:10]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([OH:31])[C@H:5]2[O:6]1

Participants

3

Reactant 1

HCID 69031670HCID 69031670, compound

Product 1

HCID 69031120HCID 69031120, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5 (14.55 g, 31.86 mmol) in methylene chloride (100 ml) was added tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene]-[benzylidine]ruthenium (VI) dichloride (270 mg, 0.32 mmol), and the reaction mixture was stirred at room temperature for 2 days. The volatiles were removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give 6 (12.83 g, 94%) as a white semi-solid; 1H NMR (400 MHz, CDCl3) δ 7.47-7.21 (m, 15H), 5.93 (dd, J=5.6, 1.6 Hz, 1H), 5.73 (d, J=5.6 Hz, 1H), 5.31 (d, J=5.6 Hz, 1H), 4.56 (d, J=5.6 Hz, 1H), 3.59 (d, J=9.2 Hz, 1H), 3.15 (d, J=9.2 Hz, 1H), 3.02 (s, 1H), 1.32 (s, 3H), 1.21 (s, 3H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-d47518b3aeeb4ff5940981618def72b7
Source dataset
uspto-grants-2008_07
Patent number
US07405214B2

Reaction notes

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