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

HRID 1754038Notes

Reaction equation

HRID 1754038 reaction equation
[OH:1][CH:2]([CH2:16][CH2:17][S:18][CH3:19])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:4].C1C=C(Cl)C=C(C(OO)=[O:28])C=1>ClCCl>[OH:1][CH:2]([CH2:16][CH2:17][S:18]([CH3:19])=[O:28])[C:3]([O:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 86689969Decyl 2-hydroxy-4-(methylthio)butanoate

Product 1

HCID 86689970Decyl 2-hydroxy-4-(methylsulfinyl)butanoateYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of decyl 2-hydroxy-4-(methylthio)butanoate (20.05 g, 69.03 mmol) in dichloromethane (300 mL) at 0° C. was added mCPBA (77%, 14.7 g, 65.6 mmol) portionwise over 30 min. The resulting mixture was allowed to warm to room temperature with stirring overnight. Another portion of mCPBA (77%, 1.4 g, 6.25 mmol) was added to the solution at 0° C. and the resulting mixture was allowed to warm to room temperature with stirring over the weekend. The reaction was washed with 10% sodium bisulfite (2×100 mL), saturated sodium bicarbonate (3×150 mL), 1N HCl (1×150 mL), and brine (1×200 mL). The organic layer was dried over magnesium sulfate, filtered and evaporated to give a crude oil. The oil was purified by silica gel chromatography with 0-6% methanol/dichloromethane to give a light yellow oil (20.61 g, 97%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.85 (t, J=6.83 Hz, 3 H) 1.10-1.37 (m, 14 H) 1.50-1.65 (m, 2 H) 1.80-1.93 (m, 1 H) 1.97-2.08 (m, 1 H) 2.52 (d, J=3.81 Hz, 3 H) 2.60-2.75 (m, 1 H) 2.75-2.91 (m, 1 H) 3.98-4.12 (m, 2 H) 4.12-4.20 (m, 1 H) 5.62 (dd, J=5.72, 2.54 Hz, 1 H). m/z 307 (MH+).

Workup

  1. temperatureto warm to room temperature
  2. stirringwith stirring over the weekend
  3. washThe reaction was washed with 10% sodium bisulfite (2×100 mL), saturated sodium bicarbonate (3×150 mL), 1N HCl (1×150 mL), and brine (1×200 mL)
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude oil
  8. customThe oil was purified by silica gel chromatography with 0-6% methanol/dichloromethane

Sources & evidence

ORD record
ord-fc9ea42fba6b49138a7c8189d68a91f7
Source dataset
uspto-grants-2015_10
Patent number
US09169203B2

Reaction notes

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