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Water → 4-Cyano-4-(2-isopropyl-7-methoxybenzoxazol-4-yl)cyclohexanone

HRID 842602
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HRID 842602 반응식
[C:1]([C:3]1([C:14]2[C:19]3[N:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[O:22][C:18]=3[C:17]([O:26][CH3:27])=[CH:16][CH:15]=2)[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].[Na+].[Cl-].O>CS(C)=O>[C:1]([C:3]1([C:14]2[C:19]3[N:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[O:22][C:18]=3[C:17]([O:26][CH3:27])=[CH:16][CH:15]=2)[CH2:8][CH2:7][C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2]
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참가 물질

5

반응물 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 22614794Methyl 5-cyano-5-(2-isopropyl-7-methoxybenzoxazol-4-yl)-2-oxocyclohexanecarboxylate2회

생성물 1

HCID 97967974-Cyano-4-(2-isopropyl-7-methoxybenzoxazol-4-yl)cyclohexanone수율 77.5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
140 °C

실험 절차

0.69 g (1.86 mmol) of methyl 5-cyano-5-(2-isopropyl-7-methoxybenzoxazol-4-yl)-2-oxocyclohexanecarboxylate (starting compound A8) is dissolved in 16 ml of DMSO, a solution of 0.73 g of NaCl in 2 ml of dist. water is added and the mixture is stirred at 140° C. for 8.5 h. After cooling the reaction mixture, it is diluted with 80 ml of dist. water and extracted with ethyl acetate, and the organic phase is separated off, dried over magnesium sulfate and concentrated to dryness in vacuo. After chromatography, the title compound (0.45 g) is obtained as a colorless solid. TLC, silica gel (glass plates), petroleum ether/ethyl acetate (7:3), Rf=0.56, m.p. 118° C.

후처리

  1. temperatureAfter cooling the reaction mixture, it
  2. additionis diluted with 80 ml of dist
  3. extractionwater and extracted with ethyl acetate
  4. customthe organic phase is separated off
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-bfd69fbee8c64b78bb92bf7726c308e3
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06376485B1

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