반응 #1880960

ord-7c04250c87944dd8b5249da28c9d67db

반응 방정식

O
water
C[Si](C)(C)I
iodotrimethylsilane
COc1cc2c(cc1OC)C(C)CC2
5,6-dimethoxy-1-methylindane
C[Si](C)(C)I
iodotrimethylsilane
CC1CCc2cc(O)c(O)cc21
1-methylindane-5,6-diol
수율 93.5%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    추출the product was extracted twice
  2. 2
    세척The combined extracts were washed with 100 ml of 40% sodium hydrogen sulfite solution, 100 ml of water and 50 ml of saturated sodium chloride solution
  3. 3
    건조dried over sodium sulfate
  4. 4
    농축concentrated on a rotary evaporator

실험 절차

Over 90 min at room temperature, 27.5 ml (202 mmol) of iodotrimethylsilane were added dropwise with stirring to a solution of 19.4 g (101 mmol) of 5,6-dimethoxy-1-methylindane in 150 ml of acetonitrile. The mixture was stirred for a further 2.5 d at room temperature, in the course of which, after 48 h, again 10 ml (73.5 mmol) of iodotrimethylsilane were added. The reaction mixture was then poured into 500 ml of water and the product was extracted twice, each time with 200 ml of ether. The combined extracts were washed with 100 ml of 40% sodium hydrogen sulfite solution, 100 ml of water and 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated on a rotary evaporator. After flash chromatography (pentane/ether, 2:1, Rf=0.28) on silica gel, 15.5 g (93%) of 1-methylindane-5,6-diol were obtained.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07022664B2uspto-grants-2006_04