Hydrochloric Acid → HCID 54720306, compound
Reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:13])[CH2:7][C:8](=[O:12])[CH2:9][CH2:10][CH3:11])[CH3:4].C([Li])CCC.[CH2:19]([O:21]C(=O)C(OCC)OCC)[CH3:20].Cl.[O:32]1CC[CH2:34][CH2:33]1>>[CH2:19]([O:21][CH:4]([O:32][CH2:33][CH3:34])[C:3]1[O:5][C:6](=[O:13])[CH:7]=[C:8]([OH:12])[C:9]=1[CH2:10][CH3:11])[CH3:20]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
A solution of sodium hydride (60% dispersion in mineral oil) in tetrahydrofurane (500 ml) was cooled at 0° C. under nitrogen. 3-oxo-hexanoic-acid ethyl ester (25 g; 158 mmol) was added dropwise and the mixture was stirred at 0° C. for 15 minutes. Butyllithium 1.6 M (99 ml; 158 mmol) was added dropwise and the mixture was stirred at 0° C. for 1 hour. Diethoxy-acetic acid ethyl ester (27.8 g; 0.178 mol) was added drop wise and the mixture was stirred at 0° C. for 1 hour. Hydrochloric acid 12 N (50 ml) was added and the mixture was stirred at room temperature for 1 hour and extracted with diethyl ether to yield 20 g (53%) of intermediate 19. The product was used without further purification in the next reaction step.
Workup
- stirringthe mixture was stirred at 0° C. for 1 hour
- stirringthe mixture was stirred at 0° C. for 1 hour
- stirringthe mixture was stirred at room temperature for 1 hour
- extractionextracted with diethyl ether
Sources & evidence
- ORD record
- ord-4170be9b5e6c4ccfb38b721bb54f036d
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115608B2
Reaction notes
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