Cornforth reagent → 3-Hydroxy-5-oxo-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl ester

HRID 1690667Notes

Reaction equation

HRID 1690667 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[CH:13][CH:12]2[CH:7]([CH2:8][CH2:9][CH2:10][CH:11]2[OH:16])[CH:6]=1)=[O:4].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:14]([OH:15])=[CH:13][CH:12]2[CH:7]([CH2:8][CH2:9][CH2:10][C:11]2=[O:16])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 669044513,5-Dihydroxy-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl ester

Product 1

HCID 669047863-Hydroxy-5-oxo-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,5-Dihydroxy-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl ester (3 g, 13.5 mmol) in DCM (100 mL) is added PDC (5.33 g, 14.2 mmol). The suspension is stirred at room temperature overnight. Upon completion of the reaction, the mixture is filtered through a short silica gel pad rinsing with DCM. After evaporation of the solvent, the crude product is obtained as light yellow solid. Recrystallization with DCM and hexanes affords 2.4 g of 3-hydroxy-5-oxo-4a,5,6,7,8,8a-hexahydro-naphthalene-2-carboxylic acid methyl ester as white crystalline solid; LC/MS calculated for [M+H]+ C12H12O4: 221.1, found: 221.1.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe mixture is filtered through a short silica gel pad
  3. washrinsing with DCM
  4. customAfter evaporation of the solvent
  5. customthe crude product is obtained as light yellow solid
  6. customRecrystallization with DCM and hexanes

Sources & evidence

ORD record
ord-c7880090aa1a4605b279c9cf69d0bd69
Source dataset
uspto-grants-2012_04
Patent number
US08153671B2

Reaction notes

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