2-Pentanone, 5-(acetyloxy)- → 4-Methyl-4-pentenyl acetate

HRID 856115

반응식

HRID 856115 반응식
[CH3:1][C:2]([CH3:5])([O-])[CH3:3].[K+].[C:7]([O:10][CH2:11][CH2:12]CC(=O)C)(=[O:9])[CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:7]([O:10][CH2:11][CH2:12][CH2:1][C:2]([CH3:5])=[CH2:3])(=[O:9])[CH3:8]

참가 물질

5

반응물 2

HCID 212582-Pentanone, 5-(acetyloxy)-HCID 23665647Potassium tert-butoxide

생성물 1

HCID 122313854-Methyl-4-pentenyl acetate수율 60.4%

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

Potassium tert-butoxide (9.4 g, 84 mmol) was added to a mixture of methyltriphenylphosphonium bromide (30 g, 84 mmol) in THF (300 ml), and the mixture was stirred at room temperature for 40 minutes. To the mixture a solution of 4-oxopentyl acetate (9.9 g, 68.8 mmol) in THF (30 ml) was gradually added dropwise while cooling in an ice-bath, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into ice water, and extracted with diethyl ether twice. The extracts were combined, washed with brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to afford 4-methyl-4-pentenyl acetate (5.9 g, yield 60.4%) as a colorless oil.

후처리

  1. temperaturewhile cooling in an ice-bath
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. extractionextracted with diethyl ether twice
  4. washwashed with brine
  5. dry with materialdried over magnesium 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=4/1)

출처 및 근거

ORD 기록
ord-20fd1cb0da5b437da272849fb0179b44
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262212B2

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