Sodium Cyanide → HCID 90409313, compound

HRID 1855074Notes

Reaction equation

HRID 1855074 reaction equation
CC1C=CC(S(O[CH2:12][C:13]23[CH2:20][CH2:19][C:16]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([CH2:17][CH2:18]2)[O:15][CH2:14]3)(=O)=O)=CC=1.[C-:34]#[N:35].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-].CS(C)=O.CCOC(C)=O>[O:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:16]12[CH2:19][CH2:20][C:13]([CH2:12][C:34]#[N:35])([CH2:18][CH2:17]1)[CH2:14][O:15]2)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 90409756HCID 90409756, compound

Product 1

HCID 90409313HCID 90409313, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of (1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzene-sulfonate (230 mg, 0.495 mmol), Bu4NI (2 mg, 4.95 μmol), and NaCN (73 mg, 1.49 mmol) in DMSO (10 mL) was stirred at 135° C. under N2 for 20 h, then cooled to rt. The reaction was diluted with EtOAc (10 ml) and washed with water (20 ml×4). The organic layer was concentrated in vacuo to give a crude brown oil, which was purified by flash chromatography (SiO2) using a gradient from 0% to 30% EtOAc/hexane (20 min) to give the title compound (150 mg, 0.470 mmol, 95% yield) as a clear oil. LCMS [M+Na]+=342.1. 1H NMR (CDCl3) δ: 7.77-7.72 (dd, J=7.7, 1.9 Hz, 1H), 7.38-7.33 (m, 2H), 7.22-7.16 (m, 1H), 7.15-7.10 (m, 2H), 7.01-6.95 (m, 2H), 6.83-6.79 (dd, J=8.0, 1.3 Hz, 1H), 3.98 (s, 2H), 2.70-2.58 (m, 2H), 2.22 (s, 2H), 2.05-1.94 (m, 2H), 1.88-1.74 (m, 4H).

Workup

  1. temperaturecooled to rt
  2. washwashed with water (20 ml×4)
  3. concentrationThe organic layer was concentrated in vacuo
  4. customto give a crude brown oil, which
  5. customwas purified by flash chromatography (SiO2)
  6. customfrom 0% to 30% EtOAc/hexane (20 min)

Sources & evidence

ORD record
ord-0b28a979f21a49f196b11415942b0ba7
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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