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Dimethylformamide → methyl 7-tert-butylcarbonylamino-4-chloro-3-formyl-2H-chromene-8-carboxylate

HRID 1778392
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인쇄 미리보기

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HRID 1778392 반응식
[C:1]([C:5]([NH:7][C:8]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]2[C:11]([C:12](=O)[CH2:13][CH2:14][O:15]2)=[CH:10][CH:9]=1)=[O:6])([CH3:4])([CH3:3])[CH3:2].CN([CH:26]=[O:27])C.P(Cl)(Cl)([Cl:30])=O>ClC=C(Cl)Cl.C(Cl)Cl>[C:1]([C:5]([NH:7][C:8]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:16]2[C:11]([C:12]([Cl:30])=[C:13]([CH:26]=[O:27])[CH2:14][O:15]2)=[CH:10][CH:9]=1)=[O:6])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

6

반응물 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychloride2회HCID 66693192Methyl 7-tert-butylcarbonylamino-4-oxochroman-8-carboxylate2회

생성물 1

HCID 86684737methyl 7-tert-butylcarbonylamino-4-chloro-3-formyl-2H-chromene-8-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 6575
Trichloroethylene
용매

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온도
60 °C

실험 절차

A suspension of methyl 7-tert-butylcarbonylamino-4-oxochroman-8-carboxylate (Intermediate 77, 1.32 g) in trichloroethylene (25 mL) was treated with DMF (1.5 mL), followed by dropwise addition of phosphorus oxychloride (0.998 g). The resultant mixture was heated at 60° C. for 2 hours. A further amount of phosphorus oxychloride (0.200 g) was added and the mixture was heated at 60° C. for 40 minutes. After cooling, the mixture was diluted with DCM and washed with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted with DCM and the combined organic layers were washed with brine, dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-25% to give methyl 7-tert-butylcarbonylamino-4-chloro-3-formyl-2H-chromene-8-carboxylate (1.175 g) as a yellow solid.

후처리

  1. temperatureAfter cooling
  2. washwashed with saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous phase was extracted with DCM
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-25%

출처 및 근거

ORD 기록
ord-e078fc4cc76940f58b34499b6204e383
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09266896B2

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