Tributylstannane → trans-1-Tributylstannyl-3-trimethylsilyloxy-1-octene
Reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[O:3][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:5]#[CH:6].[CH2:14]([SnH:18]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])/[CH:6]=[CH:5]/[CH:4]([O:3][Si:2]([CH3:12])([CH3:13])[CH3:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:24][CH2:25][CH3:26]Participants
3
Procedure
Under an argon atmosphere, 3-trimethylsilyloxy-1-octyne (47, 2.00 g, 10.08 mmol) and tributyltin hydride (2.70 mL, 10.18 mmol) were irradiated with a 275 W GE sunlamp, without solvent, for 4 h to produce 49: 1H NMR (CDCl3) δ 6.04 (d, J=18.9 Hz, 1H), 5.93 (dd, J1 =18.9 Hz, J2 =5.4 Hz, 1H), 4.04 (q, J1 =6.5 Hz, J2 =5.6 Hz, 1H), 1.52, 1.34 (2m, 26H), 0.91 (m, 12H), 0.11 (s, 9H). 1H NMR analysis revealed that 49 was only ca. 85% pure. Other isomers, presumed to be the cis-vinyl-stannane and the regioisomeric vinylstannane, could be clearly seen in the vinyl region of the NMR spectrum. The production of these impurities in this reaction has been previously described.
Sources & evidence
- ORD record
- ord-6184965d8eb443069d9e99108a9299c2
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04873360
Reaction notes
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