HCID 22405679, compound → HCID 22405678, compound

HRID 441079Notes

Reaction equation

HRID 441079 reaction equation
[O:1]=[C:2]1[C:5]([O:6][CH:7]([CH3:9])[CH3:8])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:14]=[C:13]3[CH2:29][CH2:30][CH2:31][O:32][Si](C(C)C)(C(C)C)C(C)C)[C:3]1=[O:43]>C(#N)C>[O:1]=[C:2]1[C:5]([O:6][CH:7]([CH3:9])[CH3:8])=[C:4]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[N:15]([Si:19]([CH:20]([CH3:22])[CH3:21])([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:24])[CH3:25])[CH:14]=[C:13]3[CH2:29][CH2:30][CH2:31][OH:32])[C:3]1=[O:43]

Participants

3

Reactant 1

HCID 22405679HCID 22405679, compound

Product 1

HCID 22405678HCID 22405678, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 5-[1,2-dioxo-4-(1-methylethoxy)-3-cyclobuten-3-yl]-3-(3-triisopropylsiloxypropyl)-1-triisopropylsilylindole (11) (0.315 g, 0.50 mmol) in 5 mL of acetonitrile was added 48% HF (10% in MeCN, 0.35 mL, 1.0 mmol) and the mixture was stirred at room temperature for 30 min. The reaction was then quenched with 10% aqueous Na2CO3, ethyl acetate was added and the mixture was washed (10% aq. Na2CO3, brine), dried (Na2SO4) and evaporated to give a yellow gum. Flash chromatography (SiO2 /hexane-ethyl acetate, 1:1) of this gum afforded the title compound (0.209 g, 89%) as a yellow foam: IR (neat) 3480 (br), 1782, 1735, 1585, 1390 cm- ; 1H NMR (CDCl3, 200 MHz) δ 8.43 (d, J=1.4 Hz, 1H), 7.82 (dd, J=8.7, 1.7 Hz, 1H), 7.56 (d, J=8.7 Hz, 1H), 7.10 (s, 1H), 5.64 (hept, J=6.2 Hz, 1H), 3.74 (t, J=6.4 Hz, 2H), 2.90 (t, J=7.4 Hz, 2H), 2.09-1.95 (m, 2H), 1.69 (hept, J=7.5 Hz, 3H), 1.57 (d, J=6.2 Hz, 6H), 1.14 (d, J=7.5 Hz, 18H).

Workup

  1. customThe reaction was then quenched with 10% aqueous Na2CO3, ethyl acetate
  2. additionwas added
  3. washthe mixture was washed (10% aq. Na2CO3, brine)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customto give a yellow gum

Sources & evidence

ORD record
ord-20ae4d46265242ce9801b2463f9a07fd
Source dataset
uspto-grants-1996_05
Patent number
US05521188

Reaction notes

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