Pyridine → (5-Bromopentyl)cyclohexane

HRID 654897노트

반응식

HRID 654897 반응식
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.P(Br)(Br)[Br:20]>O1CCCC1>[Br:20][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 269450Cyclohexanepentanol

생성물 1

HCID 14952366(5-Bromopentyl)cyclohexane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 5-cyclohexylpentanol (1.74 g., 10.25 mmol) and pyridine (0.94 g., 11.1 mmol) at 0° under argon was added phosphorus tribromide (1.21 g., 4.5 mmol) dropwise. The reaction mixture became viscous, therefore 25 ml tetrahydrofuran was added. This mixture was stirred for 1.5 hours at room temperature, then partitioned between ethyl ether and 5% aqueous hydrochloric acid. The organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil. Purification by flash chromatography (silica, hexane) yielded the desired alkyl halide.

후처리

  1. custompartitioned between ethyl ether and 5% aqueous hydrochloric acid
  2. washThe organic portion was washed with a 5% sodium bicarbonate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark yellow oil
  7. customPurification by flash chromatography (silica, hexane)

출처 및 근거

ORD 기록
ord-93b334b57cf84c8e8dca500a087d273c
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05134128

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