HCID 86609138, compound → HCID 86609137, compound

HRID 902358Notes

Reaction equation

HRID 902358 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]([O:16][C:17]2[C:22]([CH:23]=CC)=[CH:21][CH:20]=[C:19]([Cl:26])[C:18]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[CH:14]=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1>ClCCCl.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH:14]=[CH:23][C:22]3[C:17](=[C:18]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:33])[C:19]([Cl:26])=[CH:20][CH:21]=3)[O:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86609138HCID 86609138, compound

Product 1

HCID 86609137HCID 86609137, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (2R)-2-(2′,6-dichloro-3-(prop-1-enyl)biphenyl-2-yloxy)but-3-enyl 4-methylbenzenesulfonate (3.0 g, 5.96 mmol) in 1,2-dichloroethane (60 mL) was added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (1.5 g, 1.82 mmol) and the resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure. Purification by ISCO using a solvent gradient of 0 to 20% ethyl acetate in hexanes provided 2.15 g (78%) of ((2R)-7-chloro-8-(2-chlorophenyl)-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate as an off-white solid. MS (ESI) m/z 460.9 ([M+H]+); m/z 477.9 ([M+NH4]+).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customPurification by ISCO

Sources & evidence

ORD record
ord-b3d16bd18d724f20ad74e8d3bb1cd2d4
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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