Toluene → 6'-Bromospiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione

HRID 539268ノート

反応式

HRID 539268 の反応式
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[C:12]([O:16]C)(=O)[CH:13]=[CH2:14].[CH3:18][CH2:19]C([O-])(C)C.[K+].C1(C)C=CC=CC=1.[OH-].[K+]>CC1CCCO1.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:14][CH2:13][C:12](=[O:16])[CH2:19][CH2:18]3)[C:8]2=[O:11])=[CH:4][CH:3]=1

参加物

8

反応物 5

HCID 1140TolueneHCID 7294Methyl AcrylateHCID 14797Potassium HydroxideHCID 1397781-Indanone, 6-bromo-HCID 23683543Potassium t-amylate

生成物 1

HCID 581972056'-Bromospiro[cyclohexane-1,2'-indene]-1',4(3'H)-dione収率 75%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 73012-Methyltetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

6-Bromo-2,3-dihydro-1H-inden-1-one (800 g, 3.79 mol) and methyl acrylate (787 mL, 8.72 mol) in 2-methyl-tetrahydrofuran (4 L) were stirred at 28° C. Potassium tert-pentoxide solution in toluene (1.7 M, 2.68 L, 4.55 mol) was added dropwise keeping the temperature between 30° C. and 43° C. The mixture was stirred for 0.5 h at 25° C. Water (4 L) was added and after 10 min were KOH (383 g, 6.82 mol) added. The mixture was heated to reflux and the organic solvent was distilled off during 4 h. The mixture was cooled to 10° C., and the formed precipitate was filtered off and dried in vacuo to give the title compound (837 g, 75% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.74-1.85 (m, 2 H), 1.94 (m, 2 H), 2.34 (m, 2 H), 2.52-2.60 (m, 2 H), 3.27 (s, 2 H), 7.60 (d, 1 H), 7.79-7.83 (m, 1 H), 7.89 (m, 1 H); MS (ES+) m/z 293 [M+H]|.

後処理

  1. customthe temperature between 30° C. and 43° C
  2. additionadded
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. distillationthe organic solvent was distilled off during 4 h
  6. temperatureThe mixture was cooled to 10° C.
  7. filtrationthe formed precipitate was filtered off
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-da067e1ac7fd410dbad4f2bde5c8cc9c
出典データセット
uspto-grants-2014_10
特許番号
US08865911B2

反応ノート

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