Tetrahydrofuran → 2-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanol

HRID 384540

Reaction equation

HRID 384540 reaction equation
[C:1]1([CH:7]2[S:12][CH2:11][CH2:10][CH2:9][S:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:13]([Li])[CH2:14][CH2:15][CH3:16].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[C:18]1([CH2:19][CH:20]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[S:8][CH2:9][CH2:10][CH2:11][S:12]2)[OH:21])[CH:22]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 215472-Phenyl-1,3-dithianeHCID 178418339Butyllithium

Product 1

HCID 222719962-Phenyl-1-(2-phenyl-[1,3]-dithian-2-yl)-ethanolYield 71%

Conditions

Temperature
-30 °C

Procedure

To a solution of 2-phenyl-[1,3]-dithiane (65) (4.0 g, 20.4 mmol) in THF at −30° C. was added a 1.6 M solution of n-butyllithium in THF (15.3 mL, 24.4 mmol). After stirring for 30 minutes at −30° C., a solution of phenylacetylaldehyde (2.45 g, 20.4 mmol) in tetrahydrofuran was added dropwise at −30° C. The resulting reaction mixture was stirred for another hour at 0° C. The reaction was quenched with saturated NH4Cl solution and extracted with ethyl acetate. The combined organic extracts were washed with saturated NH4Cl solution, brine and dried over Na2SO4. After filtrating and concentrating, the crude product was purified by flash chromatography on silica gel, (25% ethyl acetate in hexanes), to afford 2.63 g (71%) of the title compound (66). 1H NMR (CDCl3, 400 MHz): δ1.97 (m, 2H), 2.23 (dd, J=4.0, 1.2 Hz, 1H), 2.43 (dd, J=13.6, 10.2 Hz, 1H), 2.77 (m, 4H), 3.02 (d, J=13.6 Hz, 1H), 4.07 (m, 1H), 7.44-7.13 (m, 8H), 8.02 (dd, J=8.4, 1.4 Hz, 2H).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for another hour at 0° C
  3. customThe reaction was quenched with saturated NH4Cl solution
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with saturated NH4Cl solution, brine
  6. dry with materialdried over Na2SO4
  7. filtrationAfter filtrating
  8. concentrationconcentrating
  9. customthe crude product was purified by flash chromatography on silica gel, (25% ethyl acetate in hexanes),

Sources & evidence

ORD record
ord-cc2c40d9238e41cc84ed50ffaa49eb67
Source dataset
uspto-grants-2013_02
Patent number
US08367722B2

Linked notes

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