(2R)-2-(2'-chloro-6-fluoro-3-(prop-1-enyl)biphenyl-2-yloxy)but-3-enyl 4-methylbenzenesulfonate → ((2R)-8-(2-chlorophenyl)-7-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

HRID 902366Notes

Reaction equation

HRID 902366 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](C=CC)=[CH:21][CH:20]=[C:19]([F:26])[C:18]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:33])[CH:14]=[CH2:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1>ClCCCl.C(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)(P(C1CCCCC1)(C1CCCCC1)C1CCCCC1)C1C=CC=CC=1.Cl[Ru]Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH:14]=[CH:15][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]([F:26])=[CH:20][CH:21]=3)[O:16]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86609142(2R)-2-(2'-chloro-6-fluoro-3-(prop-1-enyl)biphenyl-2-yloxy)but-3-enyl 4-methylbenzenesulfonate

Product 1

HCID 86609141((2R)-8-(2-chlorophenyl)-7-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonateYield 51.1%

Reagents, catalysts & solvents 2

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphaneCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Treatment of (2R)-2-(2′-chloro-6-fluoro-3-(prop-1-enyl)biphenyl-2-yloxy)but-3-enyl 4-methylbenzenesulfonate (1.5 g, 3.08 mmol) with benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium (0.50 g, 0.61 mmol) in 1,2-dichloroethane (30 mL) according to the procedure described for Example 69, Step 7 provided 0.7 g (51%) of ((2R)-8-(2-chlorophenyl)-7-fluoro-2H-chromen-2-yl)methyl 4-methylbenzene-sulfonate as a thick dark oil.

Sources & evidence

ORD record
ord-ed2713968f7d4724917ed287118712f1
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

Loading…