Triethyl phosphonoacetate → Ethyl 3-(5,6,7-trimethoxynaphthalen-2-yl)propenoate

HRID 987421노트

반응식

HRID 987421 반응식
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([CH:33]=O)=[CH:24]2>C1COCC1.C(OCC)(=O)C>[CH3:17][O:18][C:19]1[C:28]([O:29][CH3:30])=[C:27]([O:31][CH3:32])[CH:26]=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23]([CH:33]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:24]2

참가 물질

6

반응물 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 218916375,6,7-Trimethoxynaphthalene-2-carbaldehyde

생성물 1

HCID 68436859Ethyl 3-(5,6,7-trimethoxynaphthalen-2-yl)propenoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

실험 절차

55% Sodium hydride (241 mg) was suspended in THF (2.5 mL) at −10° C. under an argon atmosphere, a solution of ethyl diethylphosphonoacetate (1.23 g) in THF (5 mL) was added dropwise to the suspension, and the mixture was stirred for 30 minutes. A solution of 5,6,7-trimethoxynaphthalene-2-carboaldehyde (1.23 g) in THF (10 mL) was then added dropwise, and the mixture was stirred for 30 minutes at −10° C. and 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate, washed with 2 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2) to obtain the title compound.

후처리

  1. stirringthe mixture was stirred for 30 minutes at −10° C. and 1 hour at room temperature
  2. washwashed with 2 M hydrochloric acid, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:2)

출처 및 근거

ORD 기록
ord-76c1a10e3e284e1f8685d9ad699c4718
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06632810B2

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