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 1955718Notes

Reaction equation

HRID 1955718 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-924366e94792473ca8ea26685bda58f2
Source dataset
uspto-grants-1998_07
Patent number
US05776967

Reaction notes

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