3-t-Butyldimethylsiloxy-1-iodo-trans-1-octene → HCID 178506904, compound
Reaction equation
[O:1]([CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])/[CH:10]=[CH:11]/I)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].C([Li:22])CCC>CCCCCC>[O:1]([CH:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])/[CH:10]=[CH:11]/[Li:22])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
On the other hand, 736 mg (2 mmol) of 3-t-butyldimethylsiloxy-1-iodo-trans-1-octene was added to 2 ml. of anhydrous hexane, and 1.4 ml. (2 mmol) of a 1.4 M hexane solution of n-butyllithium was added. The mixture was stirred at -78° C. for 30 minutes in an atmosphere of nitrogen to afford an anhydrous hexane solution of 3-t-butyldimethylsiloxy-1-lithio-trans-1-octene. The resulting solution was added dropwise to the anhydrous diethyl ether solution of copper pentylide obtained previously, and the mixture was stirred at -78° C. for 30 minutes to afford a solution of an organic copper lithium compound of the following formula ##STR19##
Sources & evidence
- ORD record
- ord-e4d2d7baeda14d75bf4a83a0e574caf4
- Source dataset
- uspto-grants-1979_02
- Patent number
- US04139717
Reaction notes
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