Hexane → HCID 22398285, 화합물

HRID 1070886노트

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HRID 1070886 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 22398285HCID 22398285, 화합물수율 82%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2019061d661243d8b8bf604d92fa643e
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903132B2

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