Water → HCID 11339806, compound

HRID 1869869Notes

Reaction equation

HRID 1869869 reaction equation
C[O:2][C:3](=[O:34])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][C:15]2[CH:16]=[C:17]3[C:22](=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:24]=2)[O:21][C:20]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:19][C:18]3([CH3:33])[CH3:32])=[CH:9][CH:8]=1)([CH3:6])[CH3:5].[OH-].[K+].O>CO.O1CCCC1.C(#N)C>[CH2:30]([C:20]1([CH2:28][CH3:29])[CH2:19][C:18]([CH3:32])([CH3:33])[C:17]2[C:22](=[C:23]([CH:25]([CH3:27])[CH3:26])[CH:24]=[C:15]([C:14]#[C:13][C:10]3[CH:11]=[CH:12][C:7]([C:4]([CH3:6])([CH3:5])[C:3]([OH:34])=[O:2])=[CH:8][CH:9]=3)[CH:16]=2)[O:21]1)[CH3:31]

Participants

7

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 690761702-[4-(2,2-Diethyl-8-isopropyl-4,4-dimethyl-chroman-6-ylethynyl)-phenyl]-2-methyl-propionic acid methyl ester2×

Product 1

HCID 11339806HCID 11339806, compoundYield 52.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[4-(2,2-diethyl-8-isopropyl-4,4-dimethyl-chroman-6-ylethynyl)-phenyl]-2-methyl-propionic acid methyl ester (Intermediate 30, 0.070 g, 0.15 mmol) in methanol (3 mL) and tetrahydrofuran (0.5 mL) was treated with a 5M solution of potassium hydroxide (2 mL, 10 mmol) and the resulting reaction mixture was stirred at ambient temperature for 2 days. The volatiles were evaporated in vacuo to a residue that was neutralized with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and brine, and dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford a residue that on preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase afforded the title product as a yellow solid (0.035 g, 51%).

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo to a residue that
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a residue that on preparative reverse phase

Sources & evidence

ORD record
ord-7c7cf2fa7854427b9495380c2feaeb4e
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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