Water → Methyl 5-methoxypent-4-enoate

HRID 5991

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HRID 5991 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 551205Methyl 5-methoxypent-4-enoate수율 607.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-db15010c44024ab7b6dce45226590289
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246966

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