Sodium Hydroxide → HCID 22923634, compound

HRID 266041Notes

Reaction equation

HRID 266041 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:19])[CH2:6][CH:7]1[CH:14]2[CH2:15][CH:10]3[CH2:11][C:12]([O:17][CH3:18])([CH2:16][CH:8]1[CH2:9]3)[CH2:13]2>CO>[CH3:18][O:17][C:12]12[CH2:16][CH:8]3[CH2:9][CH:10]([CH2:15][CH:14]([CH:7]3[CH2:6][C:5]([OH:19])=[O:4])[CH2:13]1)[CH2:11]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53783732HCID 53783732, compound

Product 1

HCID 22923634HCID 22923634, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 2.5 N sodium hydroxide solution 0.13 ml was added to methanol 2 ml solution of 5-methoxy-2-adamantyl acetic acid methyl ester 50.0 mg obtained in referential example 9 and stirred at room temperature for 7 hours. Reaction mixture was concentrated in vacuo. Saturated sodium bicarbonate solution was added to the residue and washed with ether. Aqueous layer was adjused to pH 1 by adding 12 N hydrochloric acid, and extracted with ethyl acetate, then dried by adding anhydrous sodium sulfate. After removal of the drying agent, the filtrate was concentrated in vacuo to obtain the product as a mixture of stereoisomer. (a mixture of stereoisomer 1:1 measured by gas chromatography)

Workup

  1. customobtained in referential example 9
  2. customReaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionSaturated sodium bicarbonate solution was added to the residue
  5. washwashed with ether
  6. additionby adding 12 N hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. customdried
  9. additionby adding anhydrous sodium sulfate
  10. customAfter removal of the drying agent
  11. concentrationthe filtrate was concentrated in vacuo
  12. customto obtain the product
  13. additionas a mixture of stereoisomer
  14. addition(a mixture of stereoisomer 1:1

Sources & evidence

ORD record
ord-25994de9d18f40c292e6d631c897dc0c
Source dataset
uspto-grants-1997_07
Patent number
US05650406

Reaction notes

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