HCID 86609103, compound → HCID 86609102, compound

HRID 902303Notes

Reaction equation

HRID 902303 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=C/C)=[CH:21][CH:20]=[CH:19][C:18]=2[C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][C:27]=2[Cl:33])[CH:14]=[CH2:15])(=[O:10])=[O:9])=[CH:4][CH:3]=1>ClC(Cl)C.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:15][C:22]3[C:17](=[C:18]([C:26]4[C:27]([Cl:33])=[CH:28][CH:29]=[CH:30][C:31]=4[Cl:32])[CH:19]=[CH:20][CH:21]=3)[O:16]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86609103HCID 86609103, compound

Product 1

HCID 86609102HCID 86609102, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 11967259Benzylidenebis(tricyclohexylphosphine)dichlororutheniumCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (2R)-2-({2′,6′-dichloro-3-[(1E)-prop-1-enyl]-1,1′-biphenyl-2-yl}oxy)but-3-enyl 4-methylbenzenesulfonate (2.02 g, 4.01 mmol) in anhydrous dichloroethane (50 mL) at room temperature under nitrogen was added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (0.33 g, 0.401 mmol) and the reaction mixture stirred at room temperature for 20 hours and then heated to 50° C. for 45 hours. The cooled reaction mixture was concentrated to a small volume under reduced pressure and then directly pre-adsorbed onto silica gel. Purification by flash chromatography using a solvent gradient of 5 to 15% ethyl acetate in hexane afforded 1.52 g (82%) of [(2R)-8-(2,6-dichlorophenyl)-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a brown foam. MS (ESI) m/z 478 ([M+NH4]+).

Workup

  1. temperatureheated to 50° C. for 45 hours
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated to a small volume under reduced pressure
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-cdcd11f634834164af4f2e79b06e8fae
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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