Hydrogen Peroxide → [7-(Benzyloxy)-8-(3-hydroxypropyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

HRID 49256Notes

Reaction equation

HRID 49256 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@@H:13]2[O:18][C:17]3[C:19]([CH2:31][CH:32]=[CH2:33])=[C:20]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.B.[O:35]1CCCC1.C(=O)(O)[O-].[Na+].OO>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3[C:19]([CH2:31][CH2:32][CH2:33][OH:35])=[C:20]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 88025780[(2R)-8-allyl-7-(benzyloxy)-2,3-dihydro-1,4-bezodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 18546021[7-(Benzyloxy)-8-(3-hydroxypropyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.46 g (9.6 mmole) of [(2R)-8-allyl-7-(benzyloxy)-2,3-dihydro-1,4-bezodioxin-2-yl]methyl 4-methylbenzenesulfonate in 30 mL of tetrahydrofuran at 10° C. was added 21 mL (21 mmole) of 1 M borane/tetra-hydrofuran. The solution was allowed to come to room temperature and stir under nitrogen for 3 days. Saturated aqueous sodium bicarbonate (50 mL) was cautiously added, followed by 2.5 mL of 30% hydrogen peroxide. The mixture was stirred at room temperature under nitrogen for 2 hours, then it was extracted with three 60 mL portions of ether. The combined extracts were dried over magnesium sulfate, filtered and concentrated in vacuum to give 4.87 g of the (R)-enantiomer of the title compound as a colorless oil. 1H-NMR (CDCl3): doublet 7.8 δ (2H); multiplet 7.4 δ (5H); doublet 7.35 δ (2H); doublet 6.65 δ (1H); doublet 6.45 δ (1H); singlet 5.0 δ (2H); multiplet 4.45 δ (1H); multiplet 4.2 δ (3H); doublet of doublets 4.0 δ (1H); triplet 3.5 δ (2H); doublet of triplets 2.73 δ (2H); singlet 2.45 δ (3H); multiplet 1.75 δ (2H).

Workup

  1. customto come to room temperature
  2. stirringThe mixture was stirred at room temperature under nitrogen for 2 hours
  3. extractionit was extracted with three 60 mL portions of ether
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-1f483dda0a0047cdae9ce2ec8b65a115
Source dataset
uspto-grants-2004_03
Patent number
US06706736B2

Reaction notes

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