Sodium Carbonate → HCID 70161245, compound

HRID 1636769Notes

Reaction equation

HRID 1636769 reaction equation
[CH2:1]([N:4]([CH3:25])[CH2:5][CH2:6][CH2:7]/[C:8](/[CH3:24])=[CH:9]/[CH2:10][CH2:11]/[C:12](/[CH3:23])=[CH:13]/[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)[OH:15])[CH:2]=[CH2:3].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[CH2:1]([N:4]([CH3:25])[CH2:5][CH2:6][CH2:7]/[C:8](/[CH3:24])=[CH:9]/[CH2:10][CH2:11]/[C:12](/[CH3:23])=[CH:13]/[C:14]([C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1)=[O:15])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 70162635HCID 70162635, compound

Product 1

HCID 70161245HCID 70161245, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 162 mg of (2E,6E)-(RS)-10-(allyl-methyl-amino)-1-(4-bromo-phenyl)-3,7-dimethyl-deca-2,6-dien-1-ol (Ex. 57.2) in 6 ml of methylene chloride is treated in succession with 28 mg of sodium carbonate and 730 mg of manganese(IV) oxide. After stirring for 2 hrs. the mixture is filtered, concentrated and the residue is dissolved in ethanol with 28 mg of fumaric acid, evaporated and precipitated with ethyl acetate/ether. There are obtained 87 mg of (2E,6E)-10-(allyl-methyl-amino)-1-(4-bromo-phenyl)-3,7-dimethyl-deca-2,6-dien-1-one.fumarate (1:1), MS: m/e 404 (M+H+, 1Br).

Workup

  1. filtrationthe mixture is filtered
  2. concentrationconcentrated
  3. dissolutionthe residue is dissolved in ethanol with 28 mg of fumaric acid
  4. customevaporated
  5. customprecipitated with ethyl acetate/ether

Sources & evidence

ORD record
ord-687c9b700e4247439c44943762c890d3
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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