Hydrochloric Acid → 4-[3-(Ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylic acid

HRID 1784512Notes

Reaction equation

HRID 1784512 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][CH2:8][C:9]12[CH2:16][CH2:15][C:12]([C:17]([O:19]C)=[O:18])([CH2:13][CH2:14]1)[CH2:11][CH2:10]2)(=[O:5])=[O:4])[CH3:2].[OH-].[K+].Cl>CO.O>[CH2:1]([S:3]([CH2:6][CH2:7][CH2:8][C:9]12[CH2:10][CH2:11][C:12]([C:17]([OH:19])=[O:18])([CH2:13][CH2:14]1)[CH2:15][CH2:16]2)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22591697Methyl 4-[3-(ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 225916994-[3-(Ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Sulfone 11-7 (3.1 g, 10 mmol) was dissolved in 9:1 MeOH/water (50 mL) and treated with potassium hydroxide (3 g). The solution was stirred at room temperature overnight, then the mixture was acidified with 1 N HCl and extracted four times with 50 mL of methylene chloride. The organic layer was dried over anhydrous sodium sulfate and evaporated to afford 4-[3-(ethylsulfonyl)propyl]bicyclo[2.2.2]octane-1-carboxylic acid (11-8) which was used without purification in the next step. 1H NMR (500 MHz, CDCl3): δ 3.03 (2H, q, J=7 Hz), 2.94 (2H, dd, J=7.5 Hz), 1.84 (8H, m), 1.45 (8H,m), 1.30 (2H, m) ppm.

Workup

  1. extractionextracted four times with 50 mL of methylene chloride
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-5ce4bb22dcce4c04888f87d4df956e15
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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