1,2-Dichloroethane → ((2R)-8-(biphenyl-2-yl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate

HRID 902393Notes

Reaction equation

HRID 902393 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][C:20]([F:26])=[CH:19][C:18]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2C2C=CC=CC=2)[CH:14]=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH2:40][CH2:41]Cl>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:23][C:22]3[C:17](=[C:18]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=4[C:41]4[CH:40]=[CH:4][CH:3]=[CH:2][CH:1]=4)[CH:19]=[C:20]([F:26])[CH:21]=3)[O:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 86609154(2R)-2-(5-fluoro-2'-phenyl-3-(prop-1-enyl)biphenyl-2-yloxy)but-3-enyl 4-methylbenzenesulfonate

Product 1

HCID 86609153((2R)-8-(biphenyl-2-yl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonateYield 82%

Reagents, catalysts & solvents 1

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphaneCatalyst

Procedure

Treatment of (2R)-2-(5-fluoro-2′-phenyl-3-(prop-1-enyl)biphenyl-2-yloxy)but-3-enyl 4-methylbenzenesulfonate (1.8 g, 3.40 mmol) with benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium (1.0 g, 1.22 mmol) in 1,2-dichloroethane (100 mL) according to the procedure described for Example 69, Step 7 provided 1.36 g (82%) of ((2R)-8-(biphenyl-2-yl)-6-fluoro-2H-chromen-2-yl)methyl 4-methylbenzenesulfonate as a brown solid. MS (ESI) m/z 504.1 ([M+NH4]+).

Sources & evidence

ORD record
ord-60b393e731fe4d8ebdb2511951db1893
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

Loading…