Hydrochloric Acid → HCID 59511839, compound
Reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:3]=1[O:4][Si:5]([CH:12]([CH3:14])[CH3:13])([CH:9]([CH3:11])[CH3:10])[CH:6]([CH3:8])[CH3:7].CN(CCN(CCN(C)C)C)C.C([Li])CCC.[CH:38](N1CCOCC1)=[O:39].Cl>C1COCC1>[F:1][C:2]1[C:3]([O:4][Si:5]([CH:6]([CH3:7])[CH3:8])([CH:12]([CH3:13])[CH3:14])[CH:9]([CH3:11])[CH3:10])=[CH:15][C:16]([O:19][CH3:20])=[CH:17][C:18]=1[CH:38]=[O:39]Participants
Conditions
- Temperature
- -60 °C
Procedure
To a 240 ml THF solution containing 113g of (2-fluoro-5-methoxyphenoxy)triisopropylsilane and 70g of N,N,N′,N′,N″-pentamethyldiethylenetriamine there was added dropwise 150 ml of n-butyllithium (2.66 M, hexane solution) over a period of 50 minutes, at −74° C. After stirring for 3 hours at −60° C., 70 ml of N-formylmorpholine was added. The temperature of the reaction mixture was slowly raised to 6° C. Next, 1N hydrochloric acid was added to the reaction mixture while cooling on ice, and then the mixture was extracted with a mixture of hexane and t-butylmethyl ether and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (t-butyl methyl ether-heptane) to give the title compound (113.26 g) as an oil.
Workup
- customat −74° C
- temperatureThe temperature of the reaction mixture was slowly raised to 6° C
- temperaturewhile cooling on ice
- extractionthe mixture was extracted with a mixture of hexane and t-butylmethyl ether
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe desiccating agent was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (t-butyl methyl ether-heptane)
Sources & evidence
- ORD record
- ord-a044575844db4cab91a5e77619bf9b15
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928228B2
Reaction notes
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