Bromocyclopentane → Di-n-butyl cyclopentylmalonate

HRID 2299226

반응식

HRID 2299226 반응식
[H-].[Na+].[C:3]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:12])[CH2:4][C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6].[CH:18]1(Br)[CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH:18]1([CH:4]([C:5]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:6])[C:3]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[CH2:22][CH2:21][CH2:20][CH2:19]1

참가 물질

5

반응물 3

HCID 8728Bromocyclopentane2회HCID 24758Sodium hydride2회HCID 136925Propanedioic acid, dibutyl ester

생성물 1

HCID 18380099Di-n-butyl cyclopentylmalonate수율 23.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A 0.5-liter three-neck flask equipped with a stirrer was purged with nitrogen gas, and 7.2 g (0.3 mols) of sodium hydride and 250 ml of dewatered tetrahydrofuran were put thereinto in a nitrogen stream atmosphere. With stirring, the mixture was cooled to 0° C., and, while its temperature was kept cooled, 66 ml (0.3 mols) of di-n-butyl malonate was dropwise added thereto over a period of 30 minutes. After the addition, the mixture was heated up to room temperature, and 32 ml of cyclopentyl bromide was dropwise added thereto, and refluxed for 5 hours. After this was cooled to room temperature, 10 g of sodium hydride and 32 ml of cyclopentyl bromide were added thereto, and refluxed further for 8 hours. The resulting reaction mixture was washed with 200 ml of water, and subjected to distillation under reduced pressure to obtain 20 g of di-n-butyl cyclopentylmalonate. The yield was 23.5%.

후처리

  1. customA 0.5-liter three-neck flask equipped with a stirrer
  2. temperaturewhile its temperature was kept cooled
  3. additionAfter the addition
  4. temperaturethe mixture was heated up to room temperature
  5. temperaturerefluxed for 5 hours
  6. temperatureAfter this was cooled to room temperature
  7. temperaturerefluxed further for 8 hours
  8. customThe resulting reaction mixture
  9. washwas washed with 200 ml of water
  10. distillationsubjected to distillation under reduced pressure

출처 및 근거

ORD 기록
ord-609d343da9614d96b332cf876dadeb09
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06495639B1

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