2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

HRID 1955718노트

반응식

HRID 1955718 반응식
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1([CH2:20][CH3:21])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[CH2:8][CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19].ClC1C(=O)C(C#N)=C(C#N)C(=[O:31])C=1Cl>C1COCC1.O.C1COCC1>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1([CH2:20][CH3:21])[C:10]2[NH:11][C:12]3[C:17]([C:9]=2[C:8](=[O:31])[CH2:7][O:6]1)=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH3:19]

참가 물질

5

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 527310Methyl 1,8-diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate

생성물 1

HCID 11120627Methyl (1,8-diethyl-4-oxo-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

The ester produced in step A (0.5g, 1.66 mmol) was dissolved in 5 ml of a 90% THF/water solution, and to this was added 2,3-dichloro-5,6-dicyano-1,4 -benzoquinone (0.75 g, 3.3 mmol., previously dissolved in 5 ml THF). This mixture was stirred overnight. The solvent was evaporated and 50 ml of ethyl acetate was added. The organic phase was extracted sequentially with 2.5N NaOH, distilled water and brine. The organic layer was separated, dried (MgSO4) and evaporated to produce 0.56 g of crude oil. The oil was flash chromatographed using CH2Cl2 --EtOAc 98-2 as eluant to yield 0.15 g of the desired product as a solid, m.p. 187°-189° C.

후처리

  1. customThe solvent was evaporated
  2. addition50 ml of ethyl acetate was added
  3. extractionThe organic phase was extracted sequentially with 2.5N NaOH
  4. distillationdistilled water and brine
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto produce 0.56 g of crude oil
  9. customchromatographed

출처 및 근거

ORD 기록
ord-924366e94792473ca8ea26685bda58f2
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05776967

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