Butane, 1,1'-thiobis[3-methyl- → HCID 178419188, compound

HRID 865822Notes

Reaction equation

HRID 865822 reaction equation
[B:1]#B.[BH4-].[Na+].[CH2:5]([S:10][CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:6][CH:7]([CH3:9])[CH3:8]>COCCOCCOC>[BH3:1].[CH2:11]([S:10][CH2:5][CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:12][CH:13]([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 10990Butane, 1,1'-thiobis[3-methyl-HCID 4311764Sodium borohydrideHCID 6328200Diboron

Product 1

HCID 178419188HCID 178419188, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
-78 °C

Procedure

Diborane generated as described in Example 6 was passed through a bubbler containing sodium borohydride (0.1 g) in diglyme (5 ml) and a trap cooled to -78° C. was absorbed in neat diisoamyl sulfide (8.67 g, 50 mmol) at 0° C. Excess diborane was absorbed in the next bubbler containing tetrahydrofuran (10 ml) over mercury and cooled in ice water. A mercury bubbler was connected to the exit. Diborane was passed into the sulfide until the concentration of borane in THF reached 1M. Borane-diisoamyl sulfide, a colorless liquid, was stirred overnight at room temperature prior to disconnecting the bubblers and then analyzed for active hydride by a standard procedure using a water-glycerol-methanol 1:1:1 hydrolyzing mixture. Concentration 4.2M, 11B NMR, δ, -22.5 ppm.

Workup

  1. customExcess diborane was absorbed in the next bubbler
  2. additioncontaining tetrahydrofuran (10 ml) over mercury
  3. temperaturecooled in ice water

Sources & evidence

ORD record
ord-b456c2adb5c14d08b64ec9988a44d67b
Source dataset
uspto-grants-1996_10
Patent number
US05567849

Reaction notes

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