Potassium Hydroxide → 2-[4-(8-Hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-propionic acid
Reaction equation
C[O:2][C:3](=[O:29])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[C:16]3[C:21](=[C:22]([OH:24])[CH:23]=2)[O:20][C:19]([CH3:26])([CH3:25])[CH2:18][C:17]3([CH3:28])[CH3:27])=[CH:8][CH:7]=1)[CH3:5].[OH-].[K+]>CO.O1CCCC1>[OH:24][C:22]1[CH:23]=[C:14]([C:13]#[C:12][C:9]2[CH:10]=[CH:11][C:6]([CH:4]([CH3:5])[C:3]([OH:29])=[O:2])=[CH:7][CH:8]=2)[CH:15]=[C:16]2[C:21]=1[O:20][C:19]([CH3:26])([CH3:25])[CH2:18][C:17]2([CH3:27])[CH3:28]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of 2-[4-(8-hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-propionic acid methyl ester (Intermediate 22, 0.018 g, 0.046 mmol) in methanol (1 mL) and tetrahydrofuran (0.5 mL) was treated with a 2M solution of potassium hydroxide (1 mL, 2 mmol) and the resulting reaction mixture was stirred at 80° C. for 2 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 afford the title product as a yellow solid (0.017 g, 100%).
Workup
- customthe resulting reaction mixture
- customThe volatiles were evaporated in vacuo to a residue that
- extractionextracted with ethyl acetate
- washThe organic phase was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-d6f019b66c2b40fd8b240e1e376b7c3e
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07468391B2
Reaction notes
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