Sodium Hydroxide → HCID 59504698, compound

HRID 2400550Notes

Reaction equation

HRID 2400550 reaction equation
O[C:2]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH2:5][O:4][CH2:3]1.C(N(S(F)(F)[F:20])CC)C.[OH-].[Na+]>ClCCl.O>[F:20][C:2]1([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)[CH2:5][O:4][CH2:3]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 123472(Diethylamino)sulfur trifluorideHCID 59504645HCID 59504645, compound

Product 1

HCID 59504698HCID 59504698, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-(3-hydroxyoxetan-3-yl)benzonitrile (Step 1, 600 mg, 3.43 mmol) in dichloromethane (55 mL) was added dropwise N-ethyl-N-(trifluoro-λ4-sulfanyl)ethanamine (662 mg, 4.11 mmol, dissolved in 5 mL dichloromethane) at a temperature of −78° C. After 30 minutes at this temperature, the reaction mixture was rapidly warmed to −20° C. by the aid of a water/ice bath for no longer than 30 seconds whereupon NaOH (1N aq., 20 mL) was added and the reaction mixture was allowed to warm to rt. The mixture was diluted with water (150 mL) and extracted with diethyl ether (3×50 mL). The organic extract was dried with anhydrous magnesium sulfate and filtered. After evaporation of the solvent, the crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 8:1) to afford the title compound in pure form (495 mg, 82%): 1H NMR (400 MHz, CDCl3) δ 7.76 (d, 2H), 7.73 (d, 2H), 5.15 (dd, 2H), 4.81 (dd, 2H); ES-MS m/z 178 (MH)+; HPLC RT (Method F) 1.59 min.

Workup

  1. additionwas added
  2. extractionextracted with diethyl ether (3×50 mL)
  3. extractionThe organic extract
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customAfter evaporation of the solvent
  7. customthe crude product was purified by MPLC (silica, cyclohexane/ethyl acetate 8:1)

Sources & evidence

ORD record
ord-7c4a44d37b2e4155bb12f2c21680e857
Source dataset
uspto-grants-2014_08
Patent number
US08796253B2

Reaction notes

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