Furan → 2-(Tributylstannyl)furan

HRID 1604455Notes

Reaction equation

HRID 1604455 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.C([Li])CCC.[Sn:11](Cl)([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15]>C1COCC1>[CH2:20]([Sn:11]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:16][CH2:17][CH2:18][CH3:19])[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 8029FuranHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 43936882-(Tributylstannyl)furanYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A THF solution (100 mL) of furan (6.8 g) was cooled to -78° C. under N2 atmosphere. Butyl lithium (1.6 M×62.5 mL, 100 mmol) was added dropwise through dropping funnel in 1 hr. After stirred at -78° C. for 1 hr, the reaction mixture was warmed gradually to room temperature and stirred for 30 min. The mixture was again cooled to -78° C. and added dropwise a THF solution (25 mL) of Bu3SnCl (32.5 g, 100 mmol) with stirring. The mixture was warmed gradually to room temperature and stirred for 10-12 hrs and then concentrated. Distillation (92° C., 0.5 torr) yielded 31.3 g (87.7 mmol) of 2-(tributylstannyl) furan (87% yield).

Workup

  1. customin 1 hr
  2. temperaturethe reaction mixture was warmed gradually to room temperature
  3. stirringstirred for 30 min
  4. temperatureThe mixture was again cooled to -78° C.
  5. stirringwith stirring
  6. temperatureThe mixture was warmed gradually to room temperature
  7. stirringstirred for 10-12 hrs
  8. concentrationconcentrated
  9. distillationDistillation (92° C., 0.5 torr)

Sources & evidence

ORD record
ord-10310b1a264f453d863689d065edc83b
Source dataset
uspto-grants-1999_11
Patent number
US05994394

Reaction notes

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