2-Butene, 1-bromo-3-methyl- → HCID 9994105, compound

HRID 1664834Notes

Reaction equation

HRID 1664834 reaction equation
CC(C)([O-])C.[K+].[C:7]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].Br[CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:26][C:25]([CH3:27])=[CH:24][CH2:23][N:14]([C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

6

Reactant 4

HCID 700922-Butene, 1-bromo-3-methyl-HCID 279800Di-tert-butyl IminodicarboxylateHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 9994105HCID 9994105, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (52 mg, 0.46 mmol) was added to a solution of di-tert-butyl imidodicarbonate (100 mg, 0.46 mmol) in tetrahydrofuran (1 mL). After 5 min, 1-bromo-3-methylbut-2-ene (54 μL, 0.46 mmol) was added. After 3 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with saturated brine, dried over magnesium sulfate, filtered and concentrated. MS 286.2 (M+1).

Workup

  1. waitAfter 3 h
  2. extractionthe mixture was extracted with ethyl acetate (3×)
  3. washThe combined organic extracts were washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3c76964c5fa741b58f4f631ab51bb09f
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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