HCID 12082209, compound → {7-Nitro-8-[(E)-3-oxo-1-butenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl4-methylbenzenesulfonate

HRID 495403Notes

Reaction equation

HRID 495403 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]([CH:26]=O)=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH:13]2[O:18][C:17]3[C:19](/[CH:26]=[CH:17]/[C:16](=[O:15])[CH3:22])=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:16]=3[O:15][CH2:14]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 12082209HCID 12082209, compound

Product 1

HCID 21892077{7-Nitro-8-[(E)-3-oxo-1-butenyl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3.00 g (7.37 mmole) of [(2R)-8-formyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate in 250 mL of toluene was added 2.90 g (9.10 mmole) of 1-triphenylphosphorylidene-2-propanone. The mixture was stirred at room temperature under nitrogen for 5 hours, during which time some product precipitated from solution. The solvent was removed in vacuum and the crude residue was column chromatographed on silica gel with methylene chloride as eluant to give 3.0 g of the (R)-enantiomer of the title compound as a yellow solid. 1H-NMR (CDCl3): doublet 7.8 δ (2H); doublet 7.6 δ (1H); doublet 7.5 δ (2H); doublet 7.4 δ (2H); doublet 6.95 δ (1H); doublet 6.6 δ (1H); multiplet 4.5 δ (1H); doublet of doublets 4.0 δ (1H); multiplet 4.2 δ (3H); singlet 2.45 δ (3H); singlet 2.4 δ (3H).

Workup

  1. customprecipitated from solution
  2. customThe solvent was removed in vacuum
  3. customchromatographed on silica gel with methylene chloride as eluant

Sources & evidence

ORD record
ord-fab3317a39c44409893abaed6994914f
Source dataset
uspto-grants-2005_09
Patent number
US06939877B2

Reaction notes

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