Tributylstannane → HCID 12786209, compound

HRID 126718Notes

Reaction equation

HRID 126718 reaction equation
[F:1][C:2]([F:17])([F:16])[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].N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:30]([SnH:34]([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH3:33]>>[F:17][C:2]([F:1])([F:16])[C:3]([O:11][Si:12]([CH3:14])([CH3:15])[CH3:13])([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4]/[CH:5]=[CH:6]/[Sn:34]([CH2:35][CH2:36][CH2:37][CH3:38])([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:30][CH2:31][CH2:32][CH3:33]

Participants

4

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 21764788HCID 21764788, compound

Product 1

HCID 12786209HCID 12786209, compound

Procedure

A stirred mixture of 6.66 g. of 4-trifluoromethyl-4-trimethylsiloxy-1-octyne and 26 mg. of azobisisobutyronitrile, under argon, is treated with 6.95 ml. of tri-n-butyl tin hydride, via a syringe. After treatment, a condenser is attached to the reaction vessel and the reaction mixture, under argon, is slowly heated to 130°-135° C. and maintained at this temperature for 1.5 hours. Subsequent fractional distillation of the reaction mixture at approximately 0.07 mm pressure gives the desired product, b.p. 125°-135° C. (containing a minor amount of the corresponding cis isomer).

Workup

  1. additionA stirred mixture of 6.66 g
  2. temperaturethe reaction mixture, under argon, is slowly heated to 130°-135° C.
  3. temperaturemaintained at this temperature for 1.5 hours
  4. distillationSubsequent fractional distillation of the reaction mixture at approximately 0.07 mm pressure

Sources & evidence

ORD record
ord-314c7b72fc7842489d7873eac1e43453
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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