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 1955718ノート

反応式

HRID 1955718 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-924366e94792473ca8ea26685bda58f2
出典データセット
uspto-grants-1998_07
特許番号
US05776967

反応ノート

読み込み中…