HCID 14234822, compound → HCID 14234825, compound

HRID 476762Notes

Reaction equation

HRID 476762 reaction equation
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[O:10]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]3[C:21](=[CH:22][C:11]1=2)[CH2:20][CH2:19][CH2:18][C:17]3=[O:23]>C(Cl)(Cl)Cl>[Br:7][CH:18]1[CH2:19][CH2:20][C:21]2[C:16](=[CH:15][C:12]3[CH2:13][CH2:14][O:10][C:11]=3[CH:22]=2)[C:17]1=[O:23]

Participants

3

Reactant 1

HCID 14234822HCID 14234822, compound2×

Product 1

HCID 14234825HCID 14234825, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

55.33 g of pyridinium bromide perbromide are added portionwise at 0° C. to a solution of 27.1 g of 2,3,5,6,7,8-hexahydronaphtho[2,3-b]furan-5-one, the compound of Example 17, in 1.5 of chloroform. The mixture is left overnight at room temperature. The reaction mixture is then washed with water and the organic phase dried over anhydrous magnesium sulfate. Evaporation of the chloroform yields 39.85 g of a mixture which is then purified on a silica column using a mixture of methylene chloride and cyclohexane (80:20 V/V) as solvent. The product obtained is then recrystallized in ethyl acetate.

Workup

  1. washThe reaction mixture is then washed with water
  2. dry with materialthe organic phase dried over anhydrous magnesium sulfate
  3. customEvaporation of the chloroform

Sources & evidence

ORD record
ord-7b356805dd3341a69d3d055dd0eaabaf
Source dataset
uspto-grants-1989_12
Patent number
US04885373

Reaction notes

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