Sodium Hydroxide → HCID 57185439, compound

HRID 982126Notes

Reaction equation

HRID 982126 reaction equation
[C:1]([C@H:5]1[C@@H:16]2[C:17]3[C:8](=[CH:9][C:10]([O:24][CH3:25])=[CH:11][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>[CH3:25][O:24][C:10]1[CH:9]=[C:8]2[C:17]3[C@H:16]([CH2:15][C@H:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH2:13][C:12]=3[CH:11]=1)[C@H:5]([C:1]([OH:3])=[O:2])[CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56991050HCID 56991050, compound

Product 1

HCID 57185439HCID 57185439, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude [1R,8S,9aR] 1-carbomethoxy-5-methoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene (0.8 g., 2.1 mmol), from Step 4, is dissolved in 100 mL of methanol and 8 mL of 1N aqueous sodium hydroxide is added. After stirring for 3 days at ambient temperature, the methanol is removed under reduced pressure. The residue is partitioned between 50 mL of diethyl ether and 75 mL of water. The aqueous phase is acidified to pH 2 with 6M aqueous hydrochloric acid solution and the product is extracted with 3×25 mL of 1:1 ethyl acetate:diethyl ether. The combined organic layers are washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give the title compound.

Workup

  1. customthe methanol is removed under reduced pressure
  2. customThe residue is partitioned between 50 mL of diethyl ether and 75 mL of water
  3. extractionthe product is extracted with 3×25 mL of 1:1 ethyl acetate
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be2f75cb1aea4a3d8e00177807f29d0d
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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