1-Pentyne → 1-Chlorooct-4-yn-3-ol

HRID 1659022ノート

反応式

HRID 1659022 の反応式
C([Li])CCC.[CH:6]#[C:7][CH2:8][CH2:9][CH3:10].Cl[CH:12]([CH3:15])[CH:13]=[O:14].[Cl-:16].[NH4+]>CCCCCC>[Cl:16][CH2:15][CH2:12][CH:13]([OH:14])[C:6]#[C:7][CH2:8][CH2:9][CH3:10]

参加物

6

反応物 4

HCID 123091-PentyneHCID 25517Ammonium ChlorideHCID 1354402-ChloropropanalHCID 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.; λ max. 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. temperatureis maintained at 10°-15°C
  5. stirringto stir at ambient temperature for 18 hours
  6. customThe organic phase is separated
  7. washwashed
  8. additionwith dilute hydrochloric solution
  9. dry with materialdried with anhydrous magnesium sulfate
  10. distillationDistillation
  11. customgives 5.1 g

出典と根拠

ORDレコード
ord-a88cfad6576149f4a081ac99b2c25ef8
出典データセット
uspto-grants-1976_06
特許番号
US03966773

反応ノート

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