tert-Butanol → HCID 12044217, compound

HRID 882095Notes

Reaction equation

HRID 882095 reaction equation
[C:1]([OH:5])(C)([CH3:3])[CH3:2].[CH2:6]([C:8]1[CH:9]=[CH:10]C(C=C)=[N:12][CH:13]=1)[CH3:7].BrN1C(=O)CCC1=O.[OH-].[Na+]>O>[CH2:9]([C:8]1[CH:6]=[CH:7][C:2]([CH:1]2[CH2:3][O:5]2)=[N:12][CH:13]=1)[CH3:10]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 222462Pyridine, 5-ethyl-2-vinyl-

Product 1

HCID 12044217HCID 12044217, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 750 mL tert-butanol and 2250 mL water, 200 g (1.488 mol) of 5-ethyl-2-vinyl-pyridine was dissolved and under stirring 324 g (1.786 mol) N-bromosuccinimide was added in 30 min. at 25-30° C. Stirring was continued for 1 hr. and 178.6 g (4.46 mol) of NaOH dissolved in 2250 mL water was added into it. Reaction mixture was stirred for 45 min. Product was extracted twice with 1100 mL methyl tert-butyl ether. Organic layers were combined, washed with brine, dried over magnesium sulfate and concentrated in vacuo to yield 206.13 g (92%) of 6.

Workup

  1. dissolutionwas dissolved
  2. additionwas added in 30 min. at 25-30° C
  3. additionwas added into it
  4. customReaction mixture
  5. stirringwas stirred for 45 min
  6. extractionProduct was extracted twice with 1100 mL methyl tert-butyl ether
  7. washwashed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6438dd54c45644f2940c40ea2191a505
Source dataset
uspto-grants-2015_03
Patent number
US08993773B2

Reaction notes

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