Sodium Carbonate → 2-(5-Nitro-1H-indol-3-yl)ethan-1-ol

HRID 1769637Notes

Reaction equation

HRID 1769637 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([Si](C)(C)C)=[C:7]2[CH2:17][CH2:18][O:19][Si](C(C)(C)C)(C)C)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:17][CH2:18][OH:19])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 53741589HCID 53741589, compound

Product 1

HCID 119705002-(5-Nitro-1H-indol-3-yl)ethan-1-olYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-nitro-2-trimethylsilyl-3-(2-t-butyldimethylsiloxyethyl)indole (7.30 g, 0.019 mol) in 125 mL of acetonitrile was added 48% HF (3.0 mL, 0.084 mol) and the mixture was stirred at room temperature for 1 h. Another 2.5 mL (0.07 mol) of 48% HF was added and stirring was continued for 18 h. The mixture was then cautiously basified with saturated aqueous Na2CO3 and extracted with ethyl acetate. The organic extract was washed (brine), dried (Na2SO4) and evaporated to give a gum. This material was triturated with ether and the supernatant was evaporated to give a gum. Chromatography (SiO2 /hexane-ethyl acetate, 1:1) of this gum gave the title compound (2.24 g, 57%) as a solid, mp 90° C.: IR (neat) 3380 (br), 1622, 1330 cm-1 ; 1H NMR (CDCl3, 200 MHz) δ8.60 (d, J=1.7 Hz, 1 H), 8.48 (br s, 1H), 8.12 (dd, J=9.0, 1.7 Hz, 1H), 7.40 (d, J=9.0 Hz, 1H), 3.96 (t, J=6.3 Hz, 2H), 3.07 (t, J=6.3 Hz, 2H), 1.56 (s, 1H).

Workup

  1. additionAnother 2.5 mL (0.07 mol) of 48% HF was added
  2. stirringstirring
  3. waitwas continued for 18 h
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed (brine)
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customto give a gum
  10. customThis material was triturated with ether
  11. customthe supernatant was evaporated
  12. customto give a gum

Sources & evidence

ORD record
ord-d176374b05974437855eead5e2e003b4
Source dataset
uspto-grants-1995_01
Patent number
US05382592

Reaction notes

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