Tributylstannane → Z-1-tri-n-butylstannyl-3-trimethylsilyloxy-4,4-dimethyl-1-octene
Reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[O:3][CH:4]([C:7]([CH3:13])([CH3:12])[CH2:8][CH2:9][CH2:10][CH3:11])[C:5]#[CH:6].OC(C(C)(C)CCCC)C#C.C([Si](CC)(CC)OC(CCCCC)C#C)C.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:55]([SnH:59]([CH2:64][CH2:65][CH2:66][CH3:67])[CH2:60][CH2:61][CH2:62][CH3:63])[CH2:56][CH2:57][CH3:58]>>[CH2:64]([Sn:59]([CH2:55][CH2:56][CH2:57][CH3:58])([CH2:60][CH2:61][CH2:62][CH3:63])/[CH:6]=[CH:5]\[CH:4]([O:3][Si:2]([CH3:14])([CH3:15])[CH3:1])[C:7]([CH3:13])([CH3:12])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:65][CH2:66][CH3:67]Participants
Conditions
- Temperature
- 130 °C
Procedure
A mixture of 2 g (8.83 mmole) of 3-trimethylsilyloxy-4,4-dimethyl-1-octyne [prepared from 3-hydroxy-4,4-dimethyl-1-octyne U.S. Pat. No. 4,007,210 and chlorotrimethylsilane (Method of Example 1)], 10 mg of azobisisobutyronitrile and 2.09 ml (7.9 mM) of tri-n-butylstannane is stirred in an oil bath under argon atmosphere at ambient temperature and then the temperature is gradually raised to 130° C. The resulting solution is stirred at 130°-135° C. for 2 hours, then cooled to furnish Z-1-tri-n-butylstannyl-3-trimethylsilyloxy-4,4-dimethyl-1-octene. Vapor phase chromatography on a 6' 5% SE 30 column at an oven temperature of 230° C. shows a peak at retention time of 5.2 minutes. Further treatment of this solution containing the Z isomer with additional tri-n-butylstannane (3-4 mmole) and azobisisobutyronitrile (20 mg) at 130°-135° C. for 4-hour furnishes E-1-tri-n-butylstannyl-3-trimethylsilyloxy-4,4-dimethyl-1-octene. Vapor phase chromatography shows a peak at retention time of 4.7 minutes.
Workup
- temperaturecooled
Sources & evidence
- ORD record
- ord-632dacaf90e241a69e4ccab73833a8e7
- Source dataset
- uspto-grants-1980_11
- Patent number
- US04233231
Reaction notes
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