Acetic Acid → HCID 131731401, 화합물

HRID 1026648노트

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HRID 1026648 반응식
[Cl:1][C:2]1[C:14]2[CH2:13][CH2:12][C@@:11]3([CH3:15])[C@H:7]([CH2:8][N:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O)(=[O:23])C.[O-2].[Ce+4].[O-2].Br([O-])(=O)=O.[Na+]>O.O1CCOCC1>[Cl:1][C:2]1[C:14]2[C:13](=[O:23])[CH2:12][C@@:11]3([CH3:15])[C@H:7]([CH2:8][N:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 10219615Ceric oxideHCID 23668195Sodium BromateHCID 131731400HCID 131731400, 화합물

생성물 1

HCID 131731401HCID 131731401, 화합물

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매

반응 조건

온도
95 °C

실험 절차

cis-Ethyl 6-chloro-3a-methyl-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (5.55 mmol, 1630 mg) was dissolved in water (33 ml), acetic acid (8.25 ml) and 1,4-dioxane (8.25 ml). Cerium(IV) oxide (1.276 mmol, 220 mg) and sodium bromate (5.55 mmol, 837 mg) were added and the reaction mixture was heated to 95° C. for 3 hours. The reaction mixture was cooled to rt, diluted with water (30 ml) and extracted with ether. The organic extracts were dried over magnesium sulphate, filtered and the solvent removed in vacuo to give to give a crude residue that was purified by silica column chromatography (eluting with 0-60% ethyl acetate in heptane) to give cis-ethyl 6-chloro-3a-methyl-5-oxo-3,3a,4,5-tetrahydro-1H-benzo[e]isoindole-2(9bH)-carboxylate (673 mg), m/z=308.7 [M+H]+.

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with ether
  3. dry with materialThe organic extracts were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customto give
  7. customto give a crude residue that
  8. customwas purified by silica column chromatography (eluting with 0-60% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-5a98790d329e4aafbe81b68d837e4dbc
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729274B2

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