4-Toluenesulfonyl chloride → [8-Methyl-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

HRID 49244Notes

Reaction equation

HRID 49244 reaction equation
[CH3:1][C:2]1[O:16][C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:10][C@H:11]([CH2:14][OH:15])[O:12][C:13]=3[C:4]=2[CH:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:15][CH2:14][CH:11]2[CH2:10][O:9][C:8]3[CH:7]=[CH:6][C:5]4[O:16][C:2]([CH3:1])=[CH:3][C:4]=4[C:13]=3[O:12]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67550959HCID 67550959, compound

Product 1

HCID 18546017[8-Methyl-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.20 g (0.90 mmole) of [(2S)-8-methyl-2,3-dihydrofuro[3,2-f][1,4]benzodioxin-2-yl]methanol in 5.0 mL of pyridine was added 1.0 g (5.2 mmole) of p-toluenesulfonyl chloride. The mixture was stirred at room temperature under nitrogen for 15 hours. The solvent was then removed in vacuum and replaced with 200 mL of methylene chloride. The solution was washed with 100 mL portions of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuum to a brown residue. The residue was column chromatographed on silica gel with 1:1 methylene chloride/hexane as eluant and the product fractions combined and concentrated in vacuum to give 0.28 g of the (R)-enantiomer of the title compound as a pale yellow oil. 1H-NMR (CDCl3): doublet 7.79 δ (2H); doublet 7.30 δ (2H); doublet 6.86 δ (1H); doublet 6.68 δ (1H); singlet 6.29 δ (1H); multiplet 4.48 δ (1H); multiplet 4.26 δ (3H); doublet of doublets 4.06 δ (1H); singlet 2.43 δ (3H); singlet 2.41 δ (3H).

Workup

  1. customThe solvent was then removed in vacuum
  2. washThe solution was washed with 100 mL portions of 2 N aqueous HCl, saturated aqueous sodium bicarbonate and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum to a brown residue
  6. customchromatographed on silica gel with 1:1 methylene chloride/hexane as eluant
  7. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-77053314f8784463b08fe6173766e654
Source dataset
uspto-grants-2004_03
Patent number
US06706736B2

Reaction notes

Loading…