2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2,3-Dihydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate

HRID 1267251Notes

Reaction equation

HRID 1267251 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][C@H:13]2[CH2:18][O:17][C:16]3[CH:19]=[CH:20][C:21]4[O:25][CH2:24][CH2:23][C:22]=4[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][CH2:12][CH:13]2[CH2:18][O:17][C:16]3[CH:19]=[CH:20][C:21]4[O:25][CH:24]=[CH:23][C:22]=4[C:15]=3[O:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86586535(2R)-2,3,8,9-tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate

Product 1

HCID 185460202,3-Dihydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 0.54 g (0.67 mmole) of (2R)-2,3,8,9-tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate and 0.46 g (2.0 mmole) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in 20 ml of benzene was refluxed under nitrogen for 15 hours. The solvent was removed in vacuum and the residue column chromatographed on silica gel with methylene chloride as eluant. The product fractions were combined and concentrated in vacuum to give 0.40 g of the (R)-enantiomer of the of the title compound as a tan solid. 1H-NMR (CDCl3): doublet 7.8 δ (2H); doublet 7.52 δ (1H); doublet 7.3 δ (2H); doublet 6.95 δ (1H); doublet 6.8 δ (1H); doublet 6.65 δ (1H); multiplet 4.5 δ (1H); multiplet 4.25 δ (3H); doublet of doublets 4.1 δ (1H); singlet 2.4 δ (3H).

Workup

  1. customThe solvent was removed in vacuum
  2. customthe residue column chromatographed on silica gel with methylene chloride as eluant
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-a793f2fac3894996a7672f4482326797
Source dataset
uspto-grants-2003_04
Patent number
US06552049B2

Reaction notes

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