Dimethyl Sulfoxide → Cyclohexanepropionaldehyde

HRID 1423295Notes

Reaction equation

HRID 1423295 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>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

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 707633-Cyclohexyl-1-propanolHCID 81531Diisopropylethylamine

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-bc3a6e577de842efbf50e75441082f43
Source dataset
uspto-grants-2015_01
Patent number
US08927573B2

Reaction notes

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