m-Chloroperbenzoic acid → HCID 67947751, compound

HRID 1460624Notes

Reaction equation

HRID 1460624 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.C(=O)(O)[O-].[Na+].[Br:17][C@@H:18]1[C:27]([CH3:29])([CH3:28])[O:26][C:25]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[C@H:19]1[OH:30]>C(Cl)(Cl)Cl>[Br:17][C@@H:18]1[C:27]([CH3:28])([CH3:29])[O:26][C:25]2[CH:24]=[CH:23][N+:22]([O-:9])=[CH:21][C:20]=2[C@H:19]1[OH:30]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 67937472HCID 67937472, compound

Product 1

HCID 67947751HCID 67947751, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a white suspension of 7,9 mg of m-chloroperbenzoic acid and 4,4 g of dry sodiumbicarbonate in 90 ml of abs. chloroform a solution of 6,7 g of trans-3-bromo-3,4-dihydro-4-hydroxy-2,2-dimethyl-2H-pyrano[3,2-c]pyridin in 70 ml of chloroform is dropwise added under argon. After 2 hours the suspension is concentrated to dryness, the residue taken up in dichloromethane/methanol and filtrated to a clean filtrate. Concentration of the filtrate and purification by chromatography (silica gel, dichloromethan/methanol) of the residue yields solid trans-3-bromo-3,4-dihydro-4-hydroxy-2,2-dimethyl-6-oxido-2H-pyrano-[3,2-c]pyridine.

Workup

  1. concentrationAfter 2 hours the suspension is concentrated to dryness
  2. filtrationfiltrated to a clean filtrate
  3. customConcentration of the filtrate and purification by chromatography (silica gel, dichloromethan/methanol) of the residue

Sources & evidence

ORD record
ord-044757000c8e406d8908f7182450362a
Source dataset
uspto-grants-1991_12
Patent number
US05071871

Reaction notes

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