methyl (RS)-3-(1-cyclopropyl-prop-2-ynyloxy)-4,5-dimethoxy-benzoate → 2-Cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl ester

HRID 964969

반응식

HRID 964969 반응식
[CH:1]1([CH:4]([O:7][C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=2[O:18][CH3:19])[C:11]([O:13][CH3:14])=[O:12])[C:5]#[CH:6])[CH2:3][CH2:2]1>C(N(CC)C1C=CC=CC=1)C>[CH:1]1([CH:4]2[CH:5]=[CH:6][C:9]3=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:8]3[O:7]2)[CH2:3][CH2:2]1

참가 물질

3

반응물 1

HCID 54377500methyl (RS)-3-(1-cyclopropyl-prop-2-ynyloxy)-4,5-dimethoxy-benzoate

생성물 1

HCID 116449742-Cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl ester

시약·촉매·용매 1

HCID 7061N,N-Diethylaniline용매

반응 조건

온도
200 °C

실험 절차

33.5 g of methyl (RS)-3-(1-cyclopropyl-prop-2-ynyloxy)-4,5-dimethoxy-benzoate were dissolved in 330 ml of N,N-diethylaniline, heated to 200° C. under argon and stirred at 200° C. for a further 5 hrs. The solvent was distilled off at 90° C./1 mbar and the residue was extracted: 2×1.5 l of diethyl ether, 2×1.5 l of 1N HCl, 2×1.5 l of saturated NaCl. The oil obtained was purified by silica gel chromatography with toluene, then toluene/ethyl acetate 9:1. Crystallization was effected from diethyl ether and hexane. Methyl (RS)-2-cyclopropyl-7,8-dimethoxy-2H-1 -benzopyran-5-carboxylate was obtained as white crystals.

후처리

  1. distillationThe solvent was distilled off at 90° C./1 mbar
  2. extractionthe residue was extracted
  3. customThe oil obtained
  4. customwas purified by silica gel chromatography with toluene
  5. customCrystallization

출처 및 근거

ORD 기록
ord-124f22764f4c4148a869d6cfc9ecb27d
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773446

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