Hexane → HCID 22398285、化合物

HRID 1070886ノート

反応式

HRID 1070886 の反応式
[CH3:1][C:2]1([CH3:13])[C:10]2[C:5](=[CH:6][C:7]([CH3:12])=[C:8]([OH:11])[CH:9]=2)[CH2:4][CH2:3]1.[Br:14]Br.C(OCC)(=O)C.CCCCCC>C(O)(=O)C>[Br:14][C:9]1[C:8]([OH:11])=[C:7]([CH3:12])[CH:6]=[C:5]2[C:10]=1[C:2]([CH3:13])([CH3:1])[CH2:3][CH2:4]2

参加物

6

反応物 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24408BromineHCID 30175493,3,6-Trimethyl-2,3-dihydro-1H-inden-5-ol

生成物 1

HCID 22398285HCID 22398285、化合物収率 82%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

To a 25 mL one necked round bottom flask, 3,3,6-trimethylindan-5-ol was dissolved in acetic acid (10 mL). The solution was cooled down to 0° C. followed by slow addition of bromine (290 μL, 5.65 mmol). The reaction was slowly warmed up to room temperature. After 3 h of stirring, the reaction was completed. Excess acetic acid was removed by rotavap, and the residue was quenched with ascorbic acid solution. The content was extracted with sodium bicarbonate and brine. Plugged column with silica gel 5:95 ethyl acetate:hexane gave colorless oil, 4-bromo-3,3,6-trimethylindan-5-ol (82% yield). 1H NMR (300 MHz, CDCl3): δ 1.42 (s, 6H), 1.98(dd, 2H, J=15.11, 7.55 Hz), 2.24 (s, 3H), 2.54 (s, 3H), 2.57 (s, 3H), 2.85(d, 2H, J=7.55 Hz), 3.89 (s, 3H), 5.12(d, 1H, J=3.40 Hz), 6.31 (s, 1H), 6.95(m, 1H), 7.01 (s, 1H), 7.12(d, 1H, J=3.40) 8.34 (bs, 1H).

後処理

  1. temperatureThe reaction was slowly warmed up to room temperature
  2. customExcess acetic acid was removed by rotavap
  3. customthe residue was quenched with ascorbic acid solution
  4. extractionThe content was extracted with sodium bicarbonate and brine

出典と根拠

ORDレコード
ord-2019061d661243d8b8bf604d92fa643e
出典データセット
uspto-grants-2005_06
特許番号
US06903132B2

反応ノート

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