Potassium Hydroxide → (2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylic acid

HRID 2192891Notes

Reaction equation

HRID 2192891 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:16](=[CH:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:17]([O:19]CC)=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[OH-].[K+]>CO>[CH:1]1([C:4]2[CH:5]=[C:6](/[C:16](=[CH:22]\[CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)/[C:17]([OH:19])=[O:18])[CH:7]=[CH:8][C:9]=2[S:10]([CH:13]2[CH2:14][CH2:15]2)(=[O:12])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68670876ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate

Product 1

HCID 59571023(2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylic acidYield 75.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylate (3.50 g) was dissolved in methanol (42 mL), and to this solution was slowly added a 8 M aqueous potassium hydroxide solution (27 mL), which had been separately prepared. After stirring at room temperature for 3 hours, methanol was evaporated under reduced pressure, followed by careful addition of concentrated hydrochloric acid for neutralization. The resulting solid was collected by filtration, washed with water, and then dried by blowing air. The crude product was washed with diethyl ether and then dried under reduced pressure to obtain (2E)-2-[3-cyclopropyl-4-(cyclopropylsulfonyl)phenyl]-3-(tetrahydro-2H-pyran-4-yl)acrylic acid (2.47 g).

Workup

  1. customhad been separately prepared
  2. custommethanol was evaporated under reduced pressure
  3. additionfollowed by careful addition of concentrated hydrochloric acid for neutralization
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. washThe crude product was washed with diethyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-6ae4749b73d14154b2c9db96e0302ee3
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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