Water → HCID 71522687, compound

HRID 1499096Notes

Reaction equation

HRID 1499096 reaction equation
[OH:1]OS([O-])=O.[K+].[CH3:7][C:8]1([CH2:12][S:13][CH2:14][C:15]2([CH3:19])[CH2:18][O:17][CH2:16]2)[CH2:11][O:10][CH2:9]1.[OH2:20]>CO>[S:13]([CH2:12][C:8]1([CH3:7])[CH2:11][O:10][CH2:9]1)([CH2:14][C:15]1([CH3:19])[CH2:16][O:17][CH2:18]1)(=[O:1])=[O:20]

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 71522609HCID 71522609, compound

Product 1

HCID 71522687HCID 71522687, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

A suspension of oxone (650 mg, 1.06 mmol) in water (2.0 mL) was cooled to 10° C. and treated (dropwise) with a solution of 6 (108 mg, 0.533 mmol) in MeOH (2.0 mL). The solution was warmed to rt and stirred for 1 h. MeOH was removed in vacuo, and the aqueous layer was diluted with water (5 mL) and extracted with CH2C12 (4×10 mL). The combined organic layers were washed with brine (5 mL), dried (MgSO4), and concentrated in vacuo to afford the sulfone (120 mg, 96%) as a white solid: Mp 93.4-95.1° C.; IR (ATR) 2949, 2867, 1456, 1301, 1277, 967 cm−1; 1H NMR (400 MHz, CDCl3) δ 4.68 (d, J=6.4 Hz, 4H), 4.46 (d, J=6.4 Hz, 4H), 3.43 (s, 4H), 1.69 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 82.2, 62.6, 37.9, 23.3; HRMS (APCI) m/z calc for C10H19O4S (M+H) 235.1004. found 235.1032.

Workup

  1. temperatureThe solution was warmed to rt
  2. customMeOH was removed in vacuo
  3. additionthe aqueous layer was diluted with water (5 mL)
  4. extractionextracted with CH2C12 (4×10 mL)
  5. washThe combined organic layers were washed with brine (5 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c27ac82ae1c54efaaef9d557937b83de
Source dataset
uspto-grants-2015_12
Patent number
US09200035B2

Reaction notes

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