Tributylstannane → trans-3-tert-Butyldimethylsilyloxy-1-tributylstannyl-1-octene

HRID 2351794Notes

Reaction equation

[Si:1]([O:8][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:10]#[CH:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:17]([SnH:21]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>>[Si:1]([O:8][CH:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])/[CH:10]=[CH:11]/[Sn:21]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][CH3:20])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 5948Tributylstannane

HCID 11791325tert-Butyl(dimethyl)[(1-pentylprop-2-ynyl)oxy]silane

Product 1

HCID 10414672trans-3-tert-Butyldimethylsilyloxy-1-tributylstannyl-1-octene

Procedure

Irradiation of 3-(tert-butyldimethylsilyloxy)-1-octyne (48, 2.05 g, 8.53 mmol) and tributyltin hydride (2.30 mL, 8.53 mmol) under the conditions described above yielded 50: 1H NMR (CDCl3) δ 6.04 (d, J=19.0 Hz, 1H), 5.93 (dd, J1 =19.0 Hz, J2 =5.2 Hz, 1H), 4.04 (dd, J1 =6.1 Hz, J2 =5.6 Hz, 1H), 1.52, 1.34 (2m, 26H), 0.94 (m, 21H), 0.07 (s, 3H), 0.05 (s, 3H). 1H NMR analysis revealed that 50 was only 85% pure and presumably contained the same isomeric impurities as did 49.

Sources & evidence

ORD record: ord-273b7ad6dc6844a0ab32af35bd5b03d4
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04873360

Reaction notes

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