Pyridine → (5-Bromopentyl)cyclohexane

HRID 654897ノート

反応式

HRID 654897 の反応式
[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

参加物

5

反応物 3

HCID 1049PyridineHCID 24614Phosphorus tribromideHCID 269450Cyclohexanepentanol

生成物 1

HCID 14952366(5-Bromopentyl)cyclohexane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-93b334b57cf84c8e8dca500a087d273c
出典データセット
uspto-grants-1992_07
特許番号
US05134128

反応ノート

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