Sodium borohydride → Butyldiphenyltin Hydride

HRID 501917Notes

Reaction equation

HRID 501917 reaction equation
[BH4-].[Na+].[CH2:3]([Sn:7](I)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4][CH2:5][CH3:6]>C(O)C>[CH2:3]([SnH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68417447Butyl(iodo)diphenylstannane

Product 1

HCID 301705Butyldiphenyltin Hydride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

In a Schlenk tube, a suspension of NaBH4 (1.31 g, 34 mmol) in 50 mL of absolute ethanol was cooled at 0° C. under nitrogen. Then, a solution of BuSnPh2I (22.2 g) in ethanol was added slowly under stirring. After 3 hours at room temperature in the dark, petroleum ether was added, the solution was washed and dried over MgSO4. Solvents were eliminated under reduced pressure. A colourless oil was obtained (6.67 g, 0.02 mol).

Workup

  1. washthe solution was washed
  2. dry with materialdried over MgSO4
  3. customA colourless oil was obtained (6.67 g, 0.02 mol)

Sources & evidence

ORD record
ord-9e083eec9433403aaadda0b61764b698
Source dataset
uspto-grants-2010_08
Patent number
US07772417B2

Reaction notes

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