Sodium Carbonate → HCID 70162282, compound

HRID 1636765Notes

Reaction equation

HRID 1636765 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:27])[CH2:9][CH2:10]/[C:11](/[CH3:26])=[CH:12]/[CH2:13][CH2:14]/[C:15](/[CH3:25])=[CH:16]/[CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:27])[CH2:9][CH2:10]/[C:11](/[CH3:26])=[CH:12]/[CH2:13][CH2:14]/[C:15](/[CH3:25])=[CH:16]/[CH2:17][O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 70161136HCID 70161136, compound

Product 1

HCID 70162282HCID 70162282, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.4 g of (4E,8E)-1-(4-bromo-phenyl)-4,8-dimethyl-10-(tetrahydro-pyran-2-yloxy)-deca-4,8-dien-1-ol in 60 ml of methylene chloride is treated in succession with 0.29 g of sodium carbonate and 7.5 g of manganese(IV) oxide. After stirring for 3 hrs. the mixture is filtered and again treated in methylene chloride with 0.29 g of sodium carbonate and 7.5 g of manganese (IV) oxide. After filtration and silica gel chromatography with hexane/ethyl acetate (9:1) there are obtained 1.98 g of (4E,8E)-(RS)-1-(4-bromo-phenyl)-4,8-dimethyl-10-(tetrahydro-pyran-2-yloxy)-deca-4,8-dien-1-one.

Workup

  1. filtrationthe mixture is filtered
  2. additionagain treated in methylene chloride with 0.29 g of sodium carbonate and 7.5 g of manganese (IV) oxide
  3. filtrationAfter filtration and silica gel chromatography with hexane/ethyl acetate (9:1) there

Sources & evidence

ORD record
ord-50b2ddee50604765ba7460d8f11ff81e
Source dataset
uspto-grants-2000_03
Patent number
US06034275

Reaction notes

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