Furan → 5-Chloro-1-(2-furyl)-1-pentanol

HRID 1389329

反応式

HRID 1389329 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[Li].C([Li])CCC.O1C=CC=C1.[Cl:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23].[Cl-].[NH4+]>CCOCC.C(Cl)Cl.CCCCCC>[Cl:17][CH2:18][CH2:19][CH2:20][CH2:21][CH:22]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[OH:23]

参加物

9

反応物 5

HCID 8029FuranHCID 25517Ammonium ChlorideHCID 789155-Chloro-1-pentanolHCID 178418296HCID 178418296、化合物HCID 178418339Butyllithium

生成物 1

HCID 202925795-Chloro-1-(2-furyl)-1-pentanol

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒2 回HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

To a stirred suspension of 2-furyllithium (prepared from 0.53 moles of n-butyllithium and 39.5 g of furan by the procedure of J. Org. Chem., 27, 1216 (1962)) in 350 ml of ether and ca. 200 ml of hexane at -78° is added a solution of 57.9 g of 5-chloropentanol (Chem. Abstr., 59, 7579F (1963)) in 80 ml of ether during 25 minutes. The mixture is warmed to 0° during 20 minutes, stirred at 0° for 15 minutes, and treated with 140 ml of saturated ammonium chloride. The ether phase is washed with water and brine, dried over magnesium sulfate and potassum carbonate mixture, and concentrated to give a liquid, pmr spectrum (CDCl3):δ3.59 (triplet, CH2Cl2) and 4.70 (triplet, CH2CHOH).

後処理

  1. temperatureThe mixture is warmed to 0° during 20 minutes
  2. washThe ether phase is washed with water and brine
  3. dry with materialdried over magnesium sulfate and potassum carbonate mixture
  4. concentrationconcentrated
  5. customto give a liquid, pmr spectrum (CDCl3)

出典と根拠

ORDレコード
ord-36a75dccc7e641808bae0a9f004649af
出典データセット
uspto-grants-1981_01
特許番号
US04243817

関連ノート

読み込み中…