Imidazole → (S)-8-Iodo-2,6-dimethyl-2-octene

HRID 466646

반응식

HRID 466646 반응식
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@@H:7]([CH2:9][CH2:10]O)[CH3:8])[CH3:3].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:36]I>C1COCC1.CCCCCC>[I:36][CH2:10][CH2:9][C@@H:7]([CH3:8])[CH2:6][CH2:5][CH:4]=[C:2]([CH3:3])[CH3:1]

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 7793Beta-citronellol, (S)-HCID 11776Triphenylphosphine

생성물 1

HCID 11207832(S)-8-Iodo-2,6-dimethyl-2-octene수율 79.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

A solution of 3.12 g (20.0 mmol) of (S)-(-)-β-citronellol (purchased from Aldrich Chem. Co.) and 2.72 g (40.0 mmol) of imidazole in 50 mL of THF at 0° C. was treated with 5.0 g (19.5 mmol) of triphenylphosphine followed by 4.83 g (19.0 mmol) of I2 in 25 mL of THF dropwise over 20 minutes. The reaction mixture was stirred for 1.0 hour and was diluted with hexane. The organic mixture was washed with aqueous Na2SO3, brine, dried (Na2SO4) and evaporated to provide a crude white slurry. The slurry was purified by flash chromatography (300 g of silica gel) eluting with hexane to provide 4.00 g (79%) of title iodide as a colorless oil.

후처리

  1. washThe organic mixture was washed with aqueous Na2SO3, brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto provide a crude white slurry
  5. customThe slurry was purified by flash chromatography (300 g of silica gel)
  6. washeluting with hexane

출처 및 근거

ORD 기록
ord-0824be1d0c9b43e890ce4acc0d6c7a8c
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05157027

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