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

HRID 66411

반응식

HRID 66411 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.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

8

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 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

반응 조건

온도
0 °C

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 with 200 ml. of hexane at -78° C 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 mixtures is warmed to 0° C. during 20 minutes, stirred at 0° C 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 potassium carbonate mixture, and concentrated to give a liquid, pmr spectrum (CDCl3) δ 3.59 (triplet, CH2Cl) and 4.70 (triplet, CH2CHOH).

후처리

  1. additiontreated with 140 ml
  2. washThe ether phase is washed with water and brine
  3. dry with materialdried over magnesium sulfate and potassium carbonate mixture
  4. concentrationconcentrated
  5. customto give a liquid, pmr spectrum (CDCl3) δ 3.59 (triplet, CH2Cl) and 4.70 (triplet, CH2CHOH)

출처 및 근거

ORD 기록
ord-9271771fdd80462e8514c19128269368
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04131737

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