Sodium Dithionite → HCID 18434121, compound

HRID 1636766Notes

Reaction equation

HRID 1636766 reaction equation
[CH2:1]([N:4]([CH3:23])[CH2:5]/[CH:6]=[C:7](\[CH3:22])/[CH2:8][CH2:9]/[CH:10]=[C:11](\[CH3:21])/[C:12]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)=[O:13])[CH:2]=[CH2:3].C(=O)([O-])O.[Na+].[Cl-].C(C([NH3+])(C(=O)CCCCCCC)C(=O)CCCCCCC)(=O)CCCCCCC.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.O.O.CCOCC>[CH2:1]([N:4]([CH3:23])[CH2:5]/[CH:6]=[C:7](\[CH3:22])/[CH2:8][CH2:9][CH2:10][CH:11]([CH3:21])[C:12]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)=[O:13])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 24489Sodium Dithionite2×HCID 516892Sodium BicarbonateHCID 21967394HCID 21967394, compoundHCID 77620884Tricaprylylmethyl ammonium chloride

Product 1

HCID 18434121HCID 18434121, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 21584184Diethylether waterSolvent

Procedure

A solution of 188 mg of (2E,6E)-8-(allyl-methyl-amino)-1-(4-bromo-phenyl)-2,6-dimethyl-octa-2,6-dien-1-one in 4 ml of benzene is treated with a solution of 210 mg of sodium hydrogen carbonate, 61 mg of tricaprylylmethylammonium chloride and 245 mg of sodium dithionite in 4 ml of water and boiled at 80° C. for 20 min. A further 245 mg of sodium dithionite are added and, after a further 20 min. at 80° C., the mixture is worked up with water/ether. The residue is purified over silica gel with methylene chloride/methanol (2%), treated with 22 mg of fumaric acid in ethanol and concentrated. There are obtained 102 mg of (E)-(RS)-8-(allyl-methyl-amino)-1-(4-bromo-phenyl)-2,6-dimethyl-oct-6-en-1-one.fumarate (1:1), MS: m/e 376 (M-H, 1Br).

Workup

  1. customThe residue is purified over silica gel with methylene chloride/methanol (2%)
  2. additiontreated with 22 mg of fumaric acid in ethanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c171f018048c4907b0d3764d2beca055
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

Loading…