HCID 86588255, compound → HCID 11243997, compound

HRID 2084682Notes

Reaction equation

HRID 2084682 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[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH:23]=CC)[CH:14]=C)(=[O:10])=[O:9])=[CH:4][CH:3]=1>ClCCl>[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:18]3[C:17](=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:16]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86588255HCID 86588255, compound

Product 1

HCID 11243997HCID 11243997, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-{2-[1-propenyl]phenoxy}-3-butenyl 4-methyl-benzenesulfonate (3.61 g, 10.1 mmol) in dichloromethane (100 mL) is added bis(tricyclopentylphosphine)benzylidene ruthenium (IV) dichloride (1.49 g, 2.01 mmol) and the reaction mixture is stirred at room temperature for 16 hours. The solvent is removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 3:7) provides 2.48 g (78% y, >97% ee) of (2R)-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate as a pale green crystalline solid. [α]D25=+175.12 (c 9.99 in methanol, >97% ee); Rf=0.40 (silica, ethyl acetate:hexanes 3:7); Anal. Calcd. for C11H16O4S: C, 64.54; H, 5.10. Found: C, 64.85; H, 5.05.

Workup

  1. customThe solvent is removed in vacuo
  2. customto give a crude solid
  3. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 3:7)

Sources & evidence

ORD record
ord-2ffe6a12368f42129037dad32a932e1d
Source dataset
uspto-grants-2004_04
Patent number
US06716998B2

Reaction notes

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