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

HRID 1389329

반응식

HRID 1389329 반응식
[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]

참가 물질

9

반응물 5

HCID 8029FuranHCID 25517Ammonium ChlorideHCID 789155-Chloro-1-pentanolHCID 178418296HCID 178418296, 화합물HCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 3

HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-36a75dccc7e641808bae0a9f004649af
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04243817

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