HCID 23081491, compound → HCID 23081165, compound

HRID 856037Notes

Reaction equation

HRID 856037 reaction equation
[CH3:1]C(C)([O-])C.[K+].O=[C:8]([CH3:22])[CH2:9][CH2:10][CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][C:13]1=[O:21]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH3:1][C:8](=[CH2:22])[CH2:9][CH2:10][CH2:11][N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][C:13]1=[O:21]

Participants

5

Reactant 2

HCID 23081491HCID 23081491, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 23081165HCID 23081165, compoundYield 61.1%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Potassium tert-butoxide (3.5 g, 31.2 mmol) was gradually added to a mixture of methyltriphenylphosphonium bromide (11 g, 30.8 mmol) in THF (100 ml) while cooling in an ice-bath, and the mixture was stirred for 20 minutes. To which a solution of 3-(4-oxopentyl)-3H-benzoxazol-2-one (5.6 g, 25.6 mmol) in THF (10 ml) was gradually added dropwise. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water, and extracted with ethyl acetate twice. The extract was washed with water and brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1) to afford 3-(4-methyl-4-pentenyl)-3H-benzoxazol-2-one (3.4 g, yield 61%) as a colorless oil.

Workup

  1. temperaturewhile cooling in an ice-bath
  2. stirringThe resulting mixture was stirred at room temperature for 2 hours
  3. extractionextracted with ethyl acetate twice
  4. washThe extract was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-53a4c7fff4be4b7bb03015748013f77b
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…