HCID 11243997, compound → HCID 11438532, compound

HRID 2084683Notes

Reaction equation

HRID 2084683 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH:22]=[CH:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 11243997HCID 11243997, compound

Product 1

HCID 11438532HCID 11438532, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2R)-2H-chromen-2-ylmethyl 4-methylbenzenesulfonate (1.70 g, 55.00 mmol) in ethanol (100 mL) is added palladium on carbon (10 wt. %, 0.17 g) and the reaction mixture is shaken under an H2 atmosphere (50 psi) for 6 hours. The reaction mixture is filtered (celite) and the solvent removed in vacuo to provide (2R)-3,4-dihydro-2H-chromen-2-ylmethyl 4-methylbenzene-sulfonate (1.62 g, 95%) as a colorless oil which crystallizes upon standing. [α]D25=−52.69 (c 10.06 in methanol, >97% ee); Rf=0.60 (silica, ethyl acetate:hexanes 2:3); Anal. Calcd. for C17H18O4S: C, 64.13; H, 5.70. Found: C, 63.90; H, 5.71.

Workup

  1. filtrationThe reaction mixture is filtered (celite)
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a993e578094f4c61a29361be8701645c
Source dataset
uspto-grants-2004_04
Patent number
US06716998B2

Reaction notes

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