Water → Usaf DO-2

HRID 2415517Notes

Reaction equation

HRID 2415517 reaction equation
[C:1]1([CH2:7][CH:8]([C:10]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)SCCCS2)[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)C.[OH2:25]>C(OCC)(=O)C>[OH:9][CH:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 6342AcetonitrileHCID 222719962-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanol

Product 1

HCID 101556Usaf DO-2Yield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanol (66) (2.50 g, 7.9 mmol) in 100 mL of a 9:1 mixture of acetonitrile and water was added mercuric perchlorate hydrate (4.1 g, 10.3 mmol). The resulting mixture was stirred at room temperature for 5 minutes and thin layer chromatography indicated that the reaction was completed. The mixture was diluted with ethyl acetate, filtered through a pad of Celite and the filtrate was washed with saturated NaHCO3, brine and dried over Na2SO4. The solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel, (20% ethyl acetate in hexanes) to afford 1.32 g (74%) of the title compound (67). 1H NMR (CDCl3, 400 MHz): δ 2.90 (dd, J=14.4, 7.0 Hz, 1H), 3.20 (dd, J=14.4, 4.0 Hz, 1H), 3.70 (d, J=6.8 Hz, 1H), 5.35 (m, 1H), 7.28-7.11 (m, 5H), 7.53 (m, 2H), 7.93 (d, J=7.2 Hz, 2H).

Workup

  1. filtrationfiltered through a pad of Celite
  2. washthe filtrate was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was purified by flash chromatography on silica gel, (20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b5bab8c08d204e339aff1879e7f0bd3a
Source dataset
uspto-grants-2004_11
Patent number
US06818787B2

Reaction notes

Loading…