HCID 86609150, compound → HCID 86609149, compound

HRID 902384Notes

Reaction equation

HRID 902384 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]([F:26])[C:18]=2[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=2[Cl:34])[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:7]=[CH:6][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][C:30]([Cl:33])=[CH:29][C:28]=4[Cl:34])[C:19]([F:26])=[CH:20][CH:21]=3)[O:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86609150HCID 86609150, compound

Product 1

HCID 86609149HCID 86609149, compoundYield 63.5%

Reagents, catalysts & solvents 2

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

Procedure

Treatment of (2R)-2-(2′,4′-dichloro-6-fluoro-3-(prop-1-enyl)biphenyl-2-yloxy)but-3-enyl 4-methylbenzenesulfonate (0.6 g, 1.15 mmol) with benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (0.30 g, 0.36 mmol) in 1,2-dichloroethane (30 mL) according to the procedure described for Example 69, Step 7 provided 0.35 g (63%) of ((2R)-8-(2,4-dichlorophenyl)-7-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate as a brown oil.

Sources & evidence

ORD record
ord-27dd5b9fff244459994d9bd743351106
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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