Tributylstannane → HCID 12786209, compound

HRID 903672Notes

Reaction equation

HRID 903672 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].[CH2:18]([SnH:22]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH3:21]>>[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:22]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:18][CH2:19][CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 5948TributylstannaneHCID 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 azabisisobutyronitrile, 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 that 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. additionof azabisisobutyronitrile, under argon, is treated with 6.95 ml
  2. temperaturethe reaction mixture, under argon, is slowly heated to 130°-135° C.
  3. temperaturemaintained at that temperature for 1.5 hours
  4. distillationSubsequent fractional distillation of the reaction mixture at approximately 0.07 mm pressure

Sources & evidence

ORD record
ord-e933ec62c96049aab2c244df86a471b6
Source dataset
uspto-grants-1980_10
Patent number
US04228298

Reaction notes

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