Water → Methyl 5-methoxypent-4-enoate

HRID 5991

反応式

HRID 5991 の反応式
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.O=[CH:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34].O>O1CCCC1.CCCCCC>[CH3:2][O:3][CH:4]=[CH:30][CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34]

参加物

7

反応物 4

HCID 962WaterHCID 83779Methyl 4-oxobutyrateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 178418339Butyllithium

生成物 1

HCID 551205Methyl 5-methoxypent-4-enoate収率 607.8%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

34.3 g (0.1 mole) methoxymethyltriphenylphosphonium chloride was suspended in 100 ml dry tetrahydrofuran and cooled to -78° C. under argon. 75 ml (0.1 mole) n-butyllithium solution in hexane was added and the solution allowed to warm to room temperature. After cooling to -78° C. 12.1 g (0.0105 moles) methyl 4-oxobutanoate was added in 50 ml tetrahydrofuran. The solution was allowed to reach room temperature then poured into water and extracted twice with ether. The ether extracts were washed with saturated sodium chloride solution dried and concentrated in vacuo. This was eluted through 250 g silica gel with 1 l ether-hexane 1:1 to give a faintly yellow liquid 9.2 g containing both (Z) and (E) enol ethers.

後処理

  1. temperatureto warm to room temperature
  2. temperatureAfter cooling to -78° C
  3. customto reach room temperature
  4. extractionextracted twice with ether
  5. washThe ether extracts were washed with saturated sodium chloride solution
  6. customdried
  7. concentrationconcentrated in vacuo
  8. washThis was eluted through 250 g silica gel with 1 l ether-hexane 1:1

出典と根拠

ORDレコード
ord-db15010c44024ab7b6dce45226590289
出典データセット
uspto-grants-1993_09
特許番号
US05246966

関連ノート

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