Water → Usaf DO-2

HRID 554038Notes

Reaction equation

HRID 554038 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), 7.65 (m, 1H), 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-3a014e3d23ed468ba6b69c10840e0834
Source dataset
uspto-grants-2011_11
Patent number
US08048917B2

Reaction notes

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