3-Chloro-1-butyne → Ethyl 3-methyl-2-(propan-2-yl)pent-4-ynoate

HRID 905250

反応式

HRID 905250 の反応式
Cl[CH:2]([CH3:5])[C:3]#[CH:4].C[Si](C)(C)[O:8][C:9]([O:14][CH2:15][CH3:16])=[CH:10][CH:11]([CH3:13])[CH3:12].C(O)[C@H](O)[C@H]1OC(=O)C(O)=C1O>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[CH:11]([CH:10]([CH:3]([CH3:4])[C:2]#[CH:5])[C:9]([O:14][CH2:15][CH3:16])=[O:8])([CH3:13])[CH3:12]

参加物

6

反応物 3

HCID 304433-Chloro-1-butyneHCID 54010184[(1-Ethoxy-3-methylbut-1-en-1-yl)oxy](trimethyl)silaneHCID 54670067L-Ascorbic Acid

生成物 1

HCID 13227602Ethyl 3-methyl-2-(propan-2-yl)pent-4-ynoate収率 33.3%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A 250 milliliter flask was equipped with a magnetic stirrer, reflux condenser and nitrogen inlet. The flask was dried with external heat and then charged with 19.92 grams (0.22 mol) of 3-chloro-1-butyne, 30.49 grams (0.15 mol) of 1-trimethylsilyloxy-1-ethoxy-3-methylbutene prepared in Part A, 100 milliliters of dry methylene chloride, and 0.5 grams of anhydrous zinc chloride. The reaction mixture was stirred at room temperature and monitored by infrared for 48 hours. The disappearance of the ketene acetal C=C peak at 1675 cm-1 and the appearance of an ester C=O peak at 1720 cm-1 was observed. The reaction mixture was then worked up by diluting with 150 milliliters of methylene chloride and washing five times with 100 milliliters of 5% sodium bicarbonate and twice with water. The methylene chloride was dried (MgSO4) and removed under vacuum to give a residue. The residue was vacuum distilled through a vigreux column to give 8.44 grams (0.05 mol) of ethyl 2-isopropyl-3-methyl-4-pentynoate having the appearance of a colorless oil and a boiling point of 66°-76° C. at 7 millimeters pressure.

後処理

  1. customA 250 milliliter flask was equipped with a magnetic stirrer
  2. temperaturereflux condenser and nitrogen inlet
  3. customThe flask was dried
  4. temperaturewith external heat
  5. washwashing five times with 100 milliliters of 5% sodium bicarbonate
  6. dry with materialThe methylene chloride was dried (MgSO4)
  7. customremoved under vacuum
  8. customto give a residue
  9. distillationdistilled through a vigreux column

出典と根拠

ORDレコード
ord-e7a5aae0442d43df9ba0bd6df444dadb
出典データセット
uspto-grants-1983_12
特許番号
US04423064

関連ノート

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