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

HRID 66411

反応式

HRID 66411 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.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

8

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 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

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 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).

後処理

  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)

出典と根拠

ORDレコード
ord-9271771fdd80462e8514c19128269368
出典データセット
uspto-grants-1978_12
特許番号
US04131737

関連ノート

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