Hydrochloric Acid → HCID 123435007, compound
Reaction equation
[CH3:1][Si](C)(C)N[Si](C)(C)C.[Li][CH2:11][CH2:12][CH2:13][CH3:14].[SiH3:15][O:16][C:17](O[SiH3])=O.[CH2:21](Br)[C:22]#C.[C:25]1(C)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl.[CH2:33]1[CH2:37][O:36][CH2:35][CH2:34]1>CCCCCC>[CH:14]1([C:17]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([O:16][SiH3:15])[C:35](=[O:36])[CH2:34][CH2:33][C:37]#[CH:1])[CH2:22][CH2:21][CH2:11][CH2:12][CH2:13]1Participants
Conditions
- Temperature
- -5 °C
Procedure
To a stirred solution of 140 ml (0.65 moles) of hexamethyldisilazane in 1.6 L of dry THF cooled to -78° C. was added 280 ml of a 2.5M solution of n-BuLi in hexane. The mixture was stirred and warmed to -5° C. over a 0.5 hour period. The siloxy ketone (192 g, 10.632 moles) was added as a solution in 100 ml of THF and stirred at -5° C. for 1 hour. This was then added to a solution of 200 ml (1.8 moles) of 80% propargyl bromide/toluene in 800 ml THF at -78° C. The mixture was warmed slowly to room temperature over a 1 hour period, then it was poured into cold dilute hydrochloric acid and extracted with ether. The ether extracts were combined, dried, filtered and concentrated to give 216 g of a light brown oil which was used immediately in the next reaction without further purification.
Workup
- stirringstirred at -5° C. for 1 hour
- temperatureThe mixture was warmed slowly to room temperature over a 1 hour period
- extractionextracted with ether
- customdried
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e3b2ceeb02004439bb95947ab67799e1
- Source dataset
- uspto-grants-1991_07
- Patent number
- US05036107
Reaction notes
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