Benzyl mercaptan → (Benzylsulfanyl)(tributyl)stannane

HRID 1840528Notes

Reaction equation

HRID 1840528 reaction equation
CCCCCCC=CCCC.[C:12]1([CH2:18][SH:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:20]([Sn:24](Cl)([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23]>CN(C=O)C.CCCCC>[CH2:29]([Sn:24]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:25][CH2:26][CH2:27][CH3:28])[S:19][CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 15096Tributyltin ChlorideHCID 136496Undec-4-ene

Product 1

HCID 12514237(Benzylsulfanyl)(tributyl)stannaneYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8003PentaneSolvent

Conditions

Temperature
0 °C

Procedure

]undec-7-ene (DBU) is added dropwise at 20° C., under argon, to a solution of benzenemethanethiol (11.72 ml; 100.0 mmol) in anhydrous DMF (20.0 ml). After 0.5 hour at 20° C., the reaction mixture is cooled to 0° C. and tributyltin chloride is added dropwise. The mixture is allowed to warm to room temperature and stirring is continued for 5 hours. The reaction mixture is taken up in pentane (400 ml), washed with water (3×300 ml) and brine (100 ml), washed with sodium sulphate, filtered and then concentrated under reduced pressure. 39.0 g of tributyl[(phenylmethyl)thio]stannane are obtained in the form of a colourless oil, which is used without further purification in the following step.

Workup

  1. temperatureto warm to room temperature
  2. waitis continued for 5 hours
  3. washwashed with water (3×300 ml) and brine (100 ml)
  4. washwashed with sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7bbc2c1703044a6ba3458c2cbf9f1523
Source dataset
uspto-grants-2004_01
Patent number
US06680329B2

Reaction notes

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