Hydrochloric Acid → Diethyl (1-naphthyl)methylmalonate

HRID 345012

반응식

HRID 345012 반응식
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.Cl>O1CCCC1>[CH2:12]([O:11][C:3](=[O:10])[CH:4]([CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 68451-ChloromethylnaphthaleneHCID 7761Diethyl MalonateHCID 24758Sodium hydride

생성물 1

HCID 9972002Diethyl (1-naphthyl)methylmalonate수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
25 °C

실험 절차

To a suspension of sodium hydride (8 g of 60% dispersion in mineral oil, 200 mmols) in tetrahydrofuran (200 mL) was added diethyl malonate (30.5 mL, 200 mmols) dropwise over 15 minutes; gas evolution was observed. When the addition was complete, the mixture was stirred for 10 minutes at 25° C. A solution of 1-chloromethyl naphthalene (35.5 g, 200 mmols) in tetrahydrofuran (20 mL) was added dropwise over 15 minutes, after which the mixture was heated at reflux under argon for 18 hours. Excess 1N hydrochloric acid was then added and the mixture was extracted with ether. The extract was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was transferred to a flask fitted with a vacuum distillation head. Unreacted diethyl malonate (bp 45°-55° C./0.2 torr) and 1-chloromethyl naphthalene (bp 120°-130° C.) were distilled off and the residue was recooled to 25° C. The distillation residue (43.5 g) was crystallized from petroleum ether at -30° C. to give the title A compound as a low melting (mp about 30° C.) solid (27.3 g, 46%).

후처리

  1. additionWhen the addition
  2. temperatureafter which the mixture was heated
  3. temperatureat reflux under argon for 18 hours
  4. extractionthe mixture was extracted with ether
  5. washThe extract was washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was transferred to a flask
  9. customfitted with a vacuum distillation head
  10. distillationUnreacted diethyl malonate (bp 45°-55° C./0.2 torr) and 1-chloromethyl naphthalene (bp 120°-130° C.) were distilled off
  11. customwas recooled to 25° C
  12. customThe distillation residue (43.5 g) was crystallized from petroleum ether at -30° C.

출처 및 근거

ORD 기록
ord-d75bff78cd5f47a79baa48a35857844d
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055466

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