m-Chloroperbenzoic acid → Hexyl 2-hydroxy-4-(methylsulfinyl)butanoate

HRID 1754035Notes

Reaction equation

HRID 1754035 reaction equation
[OH:1][CH:2]([CH2:12][CH2:13][S:14][CH3:15])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:4].ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[OH:1][CH:2]([CH2:12][CH2:13][S:14]([CH3:15])=[O:21])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10014278Butanoic acid, 2-hydroxy-4-(methylthio)-, hexyl ester

Product 1

HCID 86689967Hexyl 2-hydroxy-4-(methylsulfinyl)butanoateYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of hexyl 2-hydroxy-4-(methylthio)butanoate (5.03 g, 21.46 mmol) in dichloromethane at 0° C. was added m-chloroperoxybenzoic acid (mCPBA) portionwise over 20 min. The resulting mixture was allowed to warm to room temperature with stirring overnight. The reaction was washed with saturated sodium bicarbonate (3×100 mL), 1N HCl (1×80 mL), and brine (1×80 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to give ˜6 g of a crude oil. The oil was purified by silica gel chromatography with 0-6% methanol/dichloromethane to give an oil (4.10 g, 76%). 1H NMR (500 MHz, chloroform-d) δ ppm 0.89 (t, J=6.68 Hz, 3 H) 1.25-1.39 (m, 6 H) 1.67 (quin, J=6.99 Hz, 2 H) 2.05-2.17 (m, 1 H) 2.32-2.42 (m, 1 H) 2.56-2.63 (m, 3 H) 2.72-2.97 (m, 2 H) 3.34-3.44 (m, 1 H) 4.15-4.24 (m, 2 H) 4.26-4.36 (m, 1 H). m/z 251 (MH+).

Workup

  1. washThe reaction was washed with saturated sodium bicarbonate (3×100 mL), 1N HCl (1×80 mL), and brine (1×80 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give ˜6 g of a crude oil
  6. customThe oil was purified by silica gel chromatography with 0-6% methanol/dichloromethane

Sources & evidence

ORD record
ord-2c9c8777a0fa474580df50f8e044f2b9
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

Loading…