Tributylstannane → HCID 12786206, compound

HRID 903384Notes

Reaction equation

HRID 903384 reaction equation
[Cl:1][CH2:2][C:3]([O:11][Si:12]([CH3:15])([CH3:14])[CH3:13])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][C:5]#[CH:6].[CH2:16]([SnH:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>>[CH2:25]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])/[CH:6]=[CH:5]/[CH2:4][C:3]([CH2:2][Cl:1])([O:11][Si:12]([CH3:15])([CH3:13])[CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])[CH2:26][CH2:27][CH3:28]

Participants

3

Reactant 2

HCID 5948TributylstannaneHCID 12786186HCID 12786186, compound

Product 1

HCID 12786206HCID 12786206, compound

Conditions

Temperature
125 °C

Procedure

A mixture of 9.27 g. of 4-chloromethyl-4-trimethylsilyloxy-1-octyne, 40 mg. of azoisobutyronitrile, and 10.0 ml. of tri-n-butyltin hydride is heated and stirred at 125° C. for 1.5 hours, then vacuum distilled through a short path to give, after a forerun, 19.5 g. of product as a colorless liquid at b.p. 140-160° C./0.1-0.2 mm.; PMR δ 5.98 (m, olefin), 3.40 (s, CH2Cl), 2.40 (m, C=C--CH2), 0.14 (s, OTMS).

Workup

  1. additionA mixture of 9.27 g
  2. distillationvacuum distilled through a short path
  3. customto give

Sources & evidence

ORD record
ord-0a52b392ea8642369ebe14c9a57637cd
Source dataset
uspto-grants-1980_10
Patent number
US04227011

Reaction notes

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