tert-Butyl isocyanate → HCID 10490186, compound

HRID 1644856Notes

Reaction equation

HRID 1644856 reaction equation
[CH2:1]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].[Li]CCCC.[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[CH2:1]([C:5]1[S:6][C:7]([C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])=[CH:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 62412tert-Butyl isocyanateHCID 5664322-IsobutylthiopheneHCID 178418339Butyllithium

Product 1

HCID 10490186HCID 10490186, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 2-iso-butylthiophene (1 g, 7.143 mmol, see step (a) above) in THF (15 mL) was added n-BuLi (1.6 M in hexane, 5.3 mL, 8.48 mmol) at −78° C. and the reaction mixture was stirred at 0° C. for 2 hours. tert-Butyl-isocyanate (897 μL, 7.86 mmol) was then added to the mixture at −78° C. The stirred solution was kept at 0° C. for an additional 2 hours. The reaction mixture was then quenched with H2O (15 mL) and extracted with EtOAc (3×20 mL). The organic layer was dried over MgSO4, concentrated and purified using silica gel column chromatography (10:90 petroleum ether-EtOAc) to give the sub-title compound (1.2 g, 5.01 mmol) as white needles in 70% yield.

Workup

  1. waitThe stirred solution was kept at 0° C. for an additional 2 hours
  2. customThe reaction mixture was then quenched with H2O (15 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-820c863369664eb3a8cd53075ed7813b
Source dataset
uspto-grants-2012_02
Patent number
US08124638B2

Reaction notes

Loading…