반응 #77532

반응 방정식

(2R)-2,3,8,9-tetrahydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-methylbenzenesulfonate

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

→

title compound

2,3-Dihydrofuro[3,2-f][1,4]benzodioxin-2-ylmethyl 4-Methylbenzenesulfonate

용매

benzene

반응 조건

후처리

1. 1
   기타The solvent was removed in vacuum
2. 2
   기타the residue column chromatographed on silica gel with methylene chloride as eluant
3. 3
   농축concentrated in vacuum

실험 절차

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 0.40g 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).

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