Acetic Acid → HCID 131731401、化合物

HRID 1026648ノート

反応式

HRID 1026648 の反応式
[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

参加物

7

反応物 4

HCID 176Acetic AcidHCID 10219615Ceric oxideHCID 23668195Sodium BromateHCID 131731400HCID 131731400、化合物

生成物 1

HCID 131731401HCID 131731401、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
95 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-5a98790d329e4aafbe81b68d837e4dbc
出典データセット
uspto-grants-2014_05
特許番号
US08729274B2

反応ノート

読み込み中…