Potassium Hydroxide → 3-[3-(8-Isopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)-phenyl]-acrylic acid
Reaction equation
C([O:3][C:4](=[O:32])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([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]([CH3:29])([CH3:28])[CH2:19][C:18]3([CH3:31])[CH3:30])[CH:8]=1)C.[OH-].[K+]>C(O)C.O1CCCC1>[CH:25]([C:23]1[CH:24]=[C:15]([C:14]#[C:13][C:9]2[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:32])=[O:3])[CH:12]=[CH:11][CH:10]=2)[CH:16]=[C:17]2[C:22]=1[O:21][C:20]([CH3:28])([CH3:29])[CH2:19][C:18]2([CH3:31])[CH3:30])([CH3:27])[CH3:26]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-[3-(8-isopropyl-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acrylic acid ethyl ester (Intermediate 33, 0.058 g, 0.13 mmol) in ethanol (2 mL) and tetrahydrofuran (2 mL) was treated with a 5N solution of potassium hydroxide (2 mL, 10 mmol) and the reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo, the residue was neutralized with dilute hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to afford the title compound (0.036 g, 66%).
Workup
- customThe volatiles were evaporated in vacuo
- extractionextracted with ethyl acetate
- washThe organic phase was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-6a958551265845e6b9297d3f47715b01
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07638648B2
Reaction notes
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