Sodium Hydroxide → [4-(8-Isopropoxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-acetic acid

HRID 2377343Notes

Reaction equation

HRID 2377343 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]3[C:20](=[C:21]([O:23][CH:24]([CH3:26])[CH3:25])[CH:22]=2)[O:19][C:18]([CH3:28])([CH3:27])[CH2:17][C:16]3([CH3:30])[CH3:29])=[CH:7][CH:6]=1.[OH-].[Na+]>CO>[CH:24]([O:23][C:21]1[CH:22]=[C:13]([C:12]#[C:11][C:8]2[CH:7]=[CH:6][C:5]([CH2:4][C:3]([OH:31])=[O:2])=[CH:10][CH:9]=2)[CH:14]=[C:15]2[C:20]=1[O:19][C:18]([CH3:27])([CH3:28])[CH2:17][C:16]2([CH3:30])[CH3:29])([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69071929[4-(8-Isopropoxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acetic acid methyl ester2×

Product 1

HCID 11361767[4-(8-Isopropoxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of [4-(8-isopropoxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-acetic acid methyl ester (Intermediate 24, 0.02 g, 0.05 mmol) in methanol (1 mL) was treated with a 2M solution of sodium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at ambient temperature for 3 h. 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 an oil. Flash column chromatography over silica gel (230-400 mesh) using 5% methanol in ethyl acetate as the eluent followed by preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase afforded the title product (0.015 g, 78%).

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 to an oil

Sources & evidence

ORD record
ord-454136b84f6642998c621fe1e9408ff9
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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