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Potassium Iodide → Methyl 4-acetyl-4-tert-butoxycarbonyl-3-dimethoxymethyl-6-nonynoate

HRID 972099
ノート
印刷プレビュー

反応式

HRID 972099 の反応式
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[C:9]([O:13][C:14]([CH:16]([C:28](=[O:30])[CH3:29])[CH:17]([CH:23]([O:26][CH3:27])[O:24][CH3:25])[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:15])([CH3:12])([CH3:11])[CH3:10].[C:31](Br)#[C:32][CH2:33][CH2:34][CH3:35]>CC(C)=O>[C:28]([C:16]([C:14]([O:13][C:9]([CH3:11])([CH3:10])[CH3:12])=[O:15])([CH2:31][C:32]#[C:33][CH2:34][CH3:35])[CH:17]([CH:23]([O:24][CH3:25])[O:26][CH3:27])[CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:30])[CH3:29]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 117687131-Bromopent-1-yneHCID 20396638Methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate

生成物 1

HCID 54174852Methyl 4-acetyl-4-tert-butoxycarbonyl-3-dimethoxymethyl-6-nonynoate

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒
2 回

実験手順

A 1.38 g quantity of potassium carbonate and 308 mg of potassium iodide are placed into a reactor. Acetone (30 ml) and a solution of 450 mg of methyl 4-tert-butoxycarbonyl-3-dimethoxymethyl-5-oxohexanoate in 10 ml of acetone are further placed into the reactor. Subsequently 270 mg of pentynyl bromide is added to the mixture. The resulting mixture is stirred at room temperature for one hour and thereafter refluxed at 70° C. for 13 hours. On completion of the reaction, the mixture is cooled to room temperature, and the solids are separated off. The product is concentrated in a vacuum, and the residue purified by a silica gel column, giving methyl 4-acetyl-4-tert-butoxycarbonyl-3-dimethoxymethyl-6-nonynoate (compound (2), R1 =t-Bu, R2 =R3 =CH3) in a yield of 91%.

後処理

  1. temperaturerefluxed at 70° C. for 13 hours
  2. customOn completion of the reaction
  3. temperaturethe mixture is cooled to room temperature
  4. customthe solids are separated off
  5. concentrationThe product is concentrated in a vacuum
  6. customthe residue purified by a silica gel column

出典と根拠

ORDレコード
ord-94d6d4b5e7f14c9cabcee09c2f2fac0e
出典データセット
uspto-grants-1979_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04163111

反応ノート

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