Hydrochloric Acid → 4-[(4E)-5-{2-[(4-tert-Butylbenzyl)oxy]phenyl}-3-(4-carboxybenzyl)pent-4-en-1-yl]benzoic acid
Reaction equation
[C:1]([C:5]1[CH:42]=[CH:41][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:31][CH2:32]C2C=CC(C#N)=CC=2)[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-:43].[K+].Cl>C(O)CC>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2/[CH:17]=[CH:18]/[CH:19]([CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[CH2:31][CH2:32][C:5]2[CH:42]=[CH:41][C:8]([C:9]([OH:10])=[O:43])=[CH:7][CH:6]=2)=[CH:41][CH:42]=1)([CH3:2])([CH3:3])[CH3:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A solution of 430 mg (0.77 mmol) of methyl 4-{(3E)4-{2-[(4-tert-butylbenzyl)oxy]phenyl}-2-[2-(4-cyanophenyl)ethyl]but-3-en-1-yl}benzoate in 20 ml of 1-propanol is mixed with 1.73 g (30.84 mmol) of potassium hydroxide and stirred at 110° C. for 5 hours. The mixture is adjusted to pH 2 with 1 M hydrochloric acid and evaporated. The resulting residue is purified directly by preparative HPLC. 290 mg (0.52 mmol, 53% yield) of the title compound are obtained.
Workup
- customevaporated
- customThe resulting residue is purified directly by preparative HPLC
Sources & evidence
- ORD record
- ord-571817d4cef74e02a9a7e0756c2f5bc5
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08609727B2
Reaction notes
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