HCID 12114961, compound → HCID 12114962, compound

HRID 433155Notes

Reaction equation

HRID 433155 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)=[CH:21][CH:20]=[CH:19][C:18]=2[O:25][CH3:26])[CH:14]=[CH2:15])(=[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:15][C:22]3[C:17](=[C:18]([O:25][CH3:26])[CH:19]=[CH:20][CH:21]=3)[O:16]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 12114961HCID 12114961, compound

Product 1

HCID 12114962HCID 12114962, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-2-(2-methoxy-6-vinylphenoxy)-3-butenyl 4-methyl-benzenesulfonate (3.00 g, 8.01 mmol) in dichloromethane (100 mL) was added bis(tricyclopentylphoshine)benzylidene ruthenium(IV) dichloride (0.59 g, 0.80 mmol) and the reaction mixture was stirred at room temperature for 4 h. The solvent was removed in vacuo to give a crude solid. Purification by flash column chromatography (silica, ethyl acetate:hexanes 2:3) provided 2.47 g (68%, >97% ee) of [(2R)-8-methoxy-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a light purple oil. [α]D5=+150.31 (c 10.18 in chloroform, >97% ee); Rf=0.53 (silica, ethyl acetate:hexanes 2:3); Anal. Calcd. for C18H18O5S.0.2 H2O: C, 61.77; H, 5.29. Found: C, 61.49; H, 5.00.

Workup

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

Sources & evidence

ORD record
ord-4e53f1e1f03247b895e17d2129378f17
Source dataset
uspto-grants-2003_12
Patent number
US06667322B2

Reaction notes

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