1,5-Dibromopentane → [4-Acetyl-3-[(5-bromopentyl)oxy]-2-propylphenoxy]acetic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([OH:16])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2].[Br:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[C:9]([O:16][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][Br:21])[C:8]=1[CH2:17][CH2:18][CH3:19])[CH3:2]Participants
5
Procedure
A mixture of 6.0 g of (4-acetyl-3-hydroxy-2-propylphenoxy)acetic acid ethyl ester, 29 ml of 1,5-dibromopentane and 2.2 g of anhydrous potassium carbonate in 150 ml of anhydrous acetone was stirred at reflux. Additional portions (2.2 g) of potassium carbonate were added at 5, 21, 29 and 38 hours. Reflux was maintained for a total of 69 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to a yellow oil which was purified by chromatography on 100 g of silica gel. Elution with 25% ethyl acetate-hexane gave 9.2 g (100%) of [4-acetyl-3-[(5-bromopentyl)oxy]-2-propylphenoxy]acetic acid ethyl ester as an oil.
Workup
- temperatureat reflux
- temperatureReflux
- temperaturewas maintained for a total of 69 hours
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated in vacuo to a yellow oil which
- customwas purified by chromatography on 100 g of silica gel
- washElution with 25% ethyl acetate-hexane
Sources & evidence
- ORD record
- ord-4bc9541ea55642698cbf73d38287a715
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04782176
Reaction notes
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