Toluene → HCID 22637068, compound

HRID 989759Notes

Reaction equation

HRID 989759 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](C=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(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:35][C:36](=[O:39])[CH2:37][CH3:38])C=CC=CC=1.[C:52]1(C)C=CC=CC=1>>[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](/[CH:38]=[CH:37]/[C:36](=[O:39])[CH2:35][CH3:52])=[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:6][CH:7]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 10980488HCID 10980488, compoundHCID 12082209HCID 12082209, compound

Product 1

HCID 22637068HCID 22637068, compound

Procedure

To a solution of 5.00 g (12.2 mmole) of [(2R)-8-formyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate in 200 mL of toluene was added 5.10 g (15.3 mmole) of 1-triphenylphosphoranylidene-2-butanone. The mixture was stirred at room temperature under nitrogen for 5 hours, after which time the solvent was removed in vacuum and the crude residue was column chromatographed on silica gel with methylene chloride as eluant to give 5.0 g of the (R)-enantiomer of the title compound as a yellow solid (m.p. 114° C.).

Workup

  1. customafter which time the solvent was removed in vacuum
  2. customchromatographed on silica gel with methylene chloride as eluant

Sources & evidence

ORD record
ord-c762cb490a334351addabbbb91aca349
Source dataset
uspto-grants-2002_10
Patent number
US06458802B1

Reaction notes

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