Dimethyl Sulfoxide → Cyclohexanepropionaldehyde

HRID 2383283Notes

Reaction equation

HRID 2383283 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS(C)=O.C(N(CC)C(C)C)(C)C.N1C=CC=CC=1.S(=O)(=O)=O>C(Cl)Cl>[CH:1]1([CH2:7][CH2:8][CH:9]=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 707633-Cyclohexyl-1-propanolHCID 81531DiisopropylethylamineHCID 168533Sulfur trioxide-pyridine

Product 1

HCID 78070CyclohexanepropionaldehydeYield 97.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Cyclohexyl-1-propanol (3.96 g, 27.8 mmol) was dissolved in DCM (90 mL) at 0° C. and treated sequentially with dimethyl sulfoxide (3.25 g, 41.7 mmol), N,N-diisopropylethylamine (8.98 g, 69.6 mmol) and sulfur trioxide pyridine-complex (11 g, 69.6 mmol). After one hour, the reaction mixture was diluted with DCM (100 mL) and washed with 1N aqueous HCl (3×50 mL), saturated sodium bicarbonate (3×50 mL), and brine. The organic layer was dried over MgSO4, filtered, and concentrated to yield the title intermediate as a light yellow oil (3.8 g). 1H NMR (d6-DMSO, 300 MHz) δ (ppm): 9.72 (s, 1H), 3.65-3.72 (m, 2H), 2.46 (t, 2H), 1.65-1.73 (m, 3H), 1.51-1.56 (m, 2H), 1.14-1.48 (m, 4H), 0.85-0.96 (m, 2H).

Workup

  1. washwashed with 1N aqueous HCl (3×50 mL), saturated sodium bicarbonate (3×50 mL), and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a1c43ed0ee074452bb9f58979c068e2b
Source dataset
uspto-grants-2012_09
Patent number
US08263618B2

Reaction notes

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