Sodium Carbonate → (2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester

HRID 12313

Reaction equation

HRID 12313 reaction equation
CC([O:4][C@@H:5]1[C:19](=[O:20])[C@H:18]2[C@@:8]([CH3:27])([CH2:9][CH2:10][C@@H:11]3[C@:17]2([CH3:21])[CH2:16][C@@H:15]([C:22]2[CH:23]=[CH:24][O:25][CH:26]=2)[O:14][C:12]3=[O:13])[C@H:7]([C:28]([O:30][CH3:31])=[O:29])[CH2:6]1)=O.C([O-])([O-])=O.[Na+].[Na+]>CO>[CH3:31][O:30][C:28]([C@@H:7]1[CH2:6][C@H:5]([OH:4])[C:19](=[O:20])[C@H:18]2[C@@:8]1([CH3:27])[CH2:9][CH2:10][C@H:11]1[C@:17]2([CH3:21])[CH2:16][C@@H:15]([C:22]2[CH:23]=[CH:24][O:25][CH:26]=2)[O:14][C:12]1=[O:13])=[O:29]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 128563Salvinorin A

Product 1

HCID 11395172(2S,4aS,6aR,7R,9S,10aS,10bR)-9-(hydroxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1 (3.5 g, 8.0 mmol) and Na2CO3 (3.4 g, 32.2 mmol) in absolute MeOH (150 mL) was stirred at room temperature for 4 b. The solvent was removed under reduced pressure and CH2Cl2 (500 mL) was added to the crude residue. The organic extract was washed successively with 2N HCl (50 mL) and saturated NaCl (50 mL) and dried (Na2SO4). The solvent was removed under reduced pressure and MeOH (100 mL) was added to the residue. The resulting solid was collected by filtration and dried to afford 2.4 g (77%) of 8a as a white solid, mp 211-214° C. (Lit. 213-216° C.).

Workup

  1. customThe solvent was removed under reduced pressure and CH2Cl2 (500 mL)
  2. additionwas added to the crude residue
  3. extractionThe organic extract
  4. washwas washed successively with 2N HCl (50 mL) and saturated NaCl (50 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under reduced pressure and MeOH (100 mL)
  7. additionwas added to the residue
  8. filtrationThe resulting solid was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-520e1e20a5b74d83883664866993db0e
Source dataset
uspto-grants-2010_06
Patent number
US07728001B2

Linked notes

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