Potassium tert-butoxide → 52856-03-8

HRID 1850106Notes

Reaction equation

HRID 1850106 reaction equation
OC(C)(C)[C:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])C)([CH3:5])[CH3:4].CC([O-])(C)C.[K+]>C1COCC1>[CH3:5][C:3]1([CH3:4])[C:9]([CH3:11])([CH3:12])[O:8][C:7](=[O:13])[NH:6]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 86659433HCID 86659433, compound

Product 1

HCID 54772352856-03-8Yield 94.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tert-butyl 3-hydroxy-2,3-dimethylbutan-2-ylcarbamate (10.02 g, 46.1 mmol) in THF (300 ml) was added portion wise potassium 2-methylpropan-2-olate (7.24 g, 64.6 mmol). The reaction was stirred for five hours and quenched with HCl (1 M, 66 mL) to pH=2. The reaction mixture was then concentrated under vacuum to about one third of the volume, and diluted with water (50 mL). The aqueous layer was then extracted with DCM (3×100 mL). The combined organic was washed with brine (50 mL), dried (Na2SO4) and concentrated to give crude product as a light tan oil (6.25 g). LCMS m/z 144.1 (M+H)+, Rt 0.42 min.

Workup

  1. customquenched with HCl (1 M, 66 mL) to pH=2
  2. concentrationThe reaction mixture was then concentrated under vacuum to about one third of the volume
  3. additiondiluted with water (50 mL)
  4. extractionThe aqueous layer was then extracted with DCM (3×100 mL)
  5. washThe combined organic was washed with brine (50 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-aa2e21400be143769a0a03bbd12831d1
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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