1-Pentyne → 1-Chlorooct-4-yn-3-ol

HRID 1439663

反応式

HRID 1439663 の反応式
C([Li])CCC.[CH:6]#[C:7][CH2:8][CH2:9][CH3:10].[Cl:11][CH2:12][CH2:13][CH:14]=[O:15].[Cl-].[NH4+]>CCCCCC>[Cl:11][CH2:12][CH2:13][CH:14]([OH:15])[C:6]#[C:7][CH2:8][CH2:9][CH3:10]

参加物

6

反応物 4

HCID 123091-PentyneHCID 25517Ammonium ChlorideHCID 29596Propanal, 3-chloro-HCID 178418339Butyllithium

生成物 1

HCID 204655481-Chlorooct-4-yn-3-ol

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒2 回

実験手順

To 68 ml. of 1.6M butyllithium in hexane at -50° C. is added dropwise, with stirring, 7.4 g. of 1-pentyne. The resulting white sludge is diluted with 20 ml. of hexane, brought to 10° C. and treated with 11 g. of freshly prepared β-chloropropionaldehyde (Org. Syn., Coll. Vol. I, p. 166) at such a rate that the temperature is maintained at 10°-15° C. The solution is allowed to stir at ambient temperature for 18 hours then treated with saturated ammonium chloride solution. The organic phase is separated, washed with dilute hydrochloric solution, dried with anhydrous magnesium sulfate and taken to dryness. Distillation gives 5.1 g. of product b.p. 65°-66° C. at 0.3 nm.; λmax. 2.95 (--OH) and 4.55 μ (--C≡C--); vapor phase chromatography shows one peak.

後処理

  1. additionThe resulting white sludge is diluted with 20 ml
  2. custombrought to 10° C.
  3. additiontreated with 11 g
  4. stirringto stir at ambient temperature for 18 hours
  5. customThe organic phase is separated
  6. washwashed
  7. additionwith dilute hydrochloric solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. distillationDistillation
  10. customgives 5.1 g

出典と根拠

ORDレコード
ord-7770def063384456aa220f3cf60b1047
出典データセット
uspto-grants-1977_11
特許番号
US04060540

関連ノート

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