HCID 86588255, compound → HCID 11243997, compound

HRID 433153Notes

Reaction equation

HRID 433153 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) was added bis(tricyclopentylphoshine)benzylidene ruthenium(IV) dichloride (1.49 g, 2.01 mmol) and the reaction mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 3:7) provided 2.48 g (78%, >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 was 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-6114f8e50d2343abb582a53f20f0c3e8
Source dataset
uspto-grants-2003_12
Patent number
US06667322B2

Reaction notes

Loading…