Triethyl phosphonoacetate → ethyl (5-fluoro-3,4-dihydro-2H-naphthalen-1-ylidene)acetate

HRID 331241노트

반응식

HRID 331241 반응식
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][CH2:22][C:23]2=O>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][CH2:22][C:23]2=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

5

반응물 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 154910385-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

생성물 1

HCID 86641631ethyl (5-fluoro-3,4-dihydro-2H-naphthalen-1-ylidene)acetate

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a suspension of 60% sodium hydride (4.12 g) in toluene (200 ml) was added dropwise ethyl diethylphosphonoacetate (20.4 ml) under ice-cooling, and the mixture was stirred at room temperature for 45 min. Then, a solution of 5-fluoro-3,4-dihydro-2H-naphthalen-1-one (15.3 g) in toluene (50 ml) was added dropwise, and the mixture was stirred at 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was poured into ice water, and the mixture was extracted with toluene. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give ethyl (5-fluoro-3,4-dihydro-2H-naphthalen-1-ylidene)acetate.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at 80° C. for 2 hr
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with toluene
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-71a0a324e50a4a0b909712235994d4e5
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877779B2

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