Water → 2,2-Dimethylpropyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl)acetate

HRID 1200191노트

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HRID 1200191 반응식
[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([OH:21])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:34][C:35]([CH3:39])([CH3:38])[CH2:36]O.O>CN(C)C=O>[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([O:21][CH2:34][C:35]([CH3:39])([CH3:38])[CH3:36])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6404Neopentyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 14650449HCID 14650449, 화합물

생성물 1

HCID 146504632,2-Dimethylpropyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl)acetate수율 23%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (2.84 g) was dissolved in dimethylformamide (30 ml) and carbodiimidazole (1.78 g) was added to the solution. After stirring at room temperature for 2 hours, 2,2-dimethyl-propanol (0.88 g) was added. After stirring at 60° C. for 4 hours, water was added and the mixture was extracted with ethyl acetate. The extracted layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography to obtain the title compound (0.82 g), yield 23%, m.p. 138°-139° C. (recrystallized from hexane-ethyl acetate).

후처리

  1. stirringAfter stirring at 60° C. for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extracted layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain
  8. customthe title compound (0.82 g), yield 23%, m.p. 138°-139° C. (recrystallized from hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-c615cf7999374561b39b79dc8b30d5df
출처 데이터셋
uspto-grants-1990_02
특허 번호
US04904690

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