Water → Butyl(triphenyl)stannane

HRID 501915

Reaction equation

HRID 501915 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[C:6]1([Sn:12](Cl)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.O>C(OCC)C>[CH2:2]([Sn:12]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 8002Butyl bromideHCID 12540Triphenyltin Chloride

Product 1

HCID 298153Butyl(triphenyl)stannaneYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

In a three-necked flask, a solution of 1-bromobutane (34.25 g, 250 mmol) in diethyl oxide was added on magnesium (7.3 g, 300 mmol) covered with dry diethyl oxide. When the addition was completed, the mixture was refluxed during one hour. This solution was then added to triphenyltin chloride (42.6 g, 110 mmol) in 150 mL of diethyl oxide and refluxed for 3 hours. The mixture was hydrolysed with a minimum of water, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulphate and concentrated. Crystallization of the crude product in methanol gave a white solid (32.3 g, 93 mmol).

Workup

  1. additionWhen the addition
  2. temperaturethe mixture was refluxed during one hour
  3. temperaturerefluxed for 3 hours
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customCrystallization of the crude product in methanol

Sources & evidence

ORD record
ord-d616d122a69e4473b00fff81be3c6f46
Source dataset
uspto-grants-2010_08
Patent number
US07772417B2

Linked notes

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