5-Methyl-2-hepten-4-one (natural) → S-(5-methyl-4-oxoheptan-2-yl) ethanethioate

HRID 708934ノート

反応式

HRID 708934 の反応式
[CH3:1][CH:2]([CH2:8][CH3:9])[C:3](=[O:7])[CH:4]=[CH:5][CH3:6].[C:10]([OH:13])(=[S:12])[CH3:11]>N1CCCCC1>[C:10](=[O:13])([S:12][CH:5]([CH2:4][C:3](=[O:7])[CH:2]([CH3:1])[CH2:8][CH3:9])[CH3:6])[CH3:11]

参加物

4

反応物 2

HCID 5177915-Methyl-2-hepten-4-one (natural)HCID 178418634HCID 178418634、化合物

生成物 1

HCID 86723328S-(5-methyl-4-oxoheptan-2-yl) ethanethioate収率 90%

試薬・触媒・溶媒 1

HCID 8082Piperidine触媒

反応条件

温度
15 °C

実験手順

A reaction flask was charged with 5-methyl-2-hepten-4-one (200 g, 1.59 mol) and piperidine (6.6 g), and cooled to 15° C. using a cooling bath. Thioacetic acid (241 g, 3.17 mol) was subsequently added to the reaction flask dropwise through an addition funnel The feeding was exothermic. The reaction temperature was kept below 25° C. After the addition was completed, the cooling bath was removed while the reaction was stirred for another hour at room temperature. The reaction mixture was then transferred into a separatory funnel. The organic layer was washed with sodium bicarbonate solution (10%, 250 mL) followed by brine (250 mL), and dried with magnesium sulfate. Further distillation of the obtained crude product under a vacuum (at 78° C. with a pressure of 11.0 mmHg) provided S-(5-methyl-4-oxoheptan-2-yl) ethanethioate (288.0 g) (about 90% yield with a purity over 97% monitored with gas chromatography).

後処理

  1. customwas kept below 25° C
  2. additionAfter the addition
  3. customthe cooling bath was removed while the reaction
  4. customThe reaction mixture was then transferred into a separatory funnel
  5. washThe organic layer was washed with sodium bicarbonate solution (10%, 250 mL)
  6. dry with materialdried with magnesium sulfate
  7. distillationFurther distillation of the
  8. customobtained crude product under a vacuum (at 78° C. with a pressure of 11.0 mmHg)

出典と根拠

ORDレコード
ord-a5e004f3da4b40b7a4e7c220e8fcf4f9
出典データセット
uspto-grants-2015_11
特許番号
US09179701B2

反応ノート

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