Sodium Hydroxide → [1R*,8S*,9aR*]5,6-Dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene-1-carboxylic acid

HRID 1089027Notes

Reaction equation

HRID 1089027 reaction equation
[C:1]([C@H:5]1[C@@H:16]2[C:17]3[C:8](=[CH:9][C:10]([O:26][CH3:27])=[C:11]([O:24][CH3:25])[C:12]=3[CH2:13][C@@H:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15]2)[CH2:7][CH2:6]1)([O:3]C)=[O:2].[OH-].[Na+]>CO>[CH3:27][O:26][C:10]1[CH:9]=[C:8]2[C:17]3[C@H:16]([CH2:15][C@H:14]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:13][C:12]=3[C:11]=1[O:24][CH3:25])[C@H:5]([C:1]([OH:3])=[O:2])[CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18641660[1R*,8S*,9aR*]1-Carbomethoxy-5,6-dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene

Product 1

HCID 18641661[1R*,8S*,9aR*]5,6-Dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene-1-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude [1R,8S,9aR]-1-carbomethoxy-5,6 dimethoxy 2,3,7,8,9,9a-hexahydro-8-phenyl-phenalene (0.8 g, 2.1 mmol) from Step 4, was dissolved in 100 mL of methanol and 8 mL of 1N aqueous sodium hydroxide was added. After stirring for 3 days at ambient temperature, the methanol was removed from the reaction mixture under reduced pressure. The residue was partitioned between 50 mL of diethyl ether and 75 mL of water. The aqueous phase was acidified to pH 2 with 6M hydrochloric acid solution and extracted with 3×25 mL of 1:1 ethyl acetate:diethyl ether. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 0.74 g (100% yield) of the title compound as an oil. DCI MS: (M+H)+ 253. 1H NMR (CDCl3) delta 2.0-2.3 (m, 2H), 2.65-2.85 (m, 2H), 2.9-3.1 (m, 6H), 3.2-3.3 (m, 1H), 3.73 (s, 3H), 3.83 (s, 3H), 6.56 (s, 1H), 7.2-7.4 (m, 5H).

Workup

  1. customthe methanol was removed from the reaction mixture under reduced pressure
  2. customThe residue was partitioned between 50 mL of diethyl ether and 75 mL of water
  3. extractionextracted with 3×25 mL of 1:1 ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5867955fe1c9471495e1eef5dc08f6f2
Source dataset
uspto-grants-1990_10
Patent number
US04963568

Reaction notes

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