Water → (S)-5-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one p-toluenesulfonate

HRID 2257235Notes

Reaction equation

HRID 2257235 reaction equation
[OH:1][CH2:2][CH2:3][C@@H:4]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C:5]1=[O:11].[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.O>N1C=CC=CC=1>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([OH:1])(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH:1][CH2:2][CH2:3][C@@H:4]1[O:8][C:7]([CH3:9])([CH3:10])[O:6][C:5]1=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 10975778(S)-5-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one

Product 1

HCID 86749377(S)-5-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-one p-toluenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
-4 °C

Procedure

Dried (S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane-4-one (9.0 g, 59.2 mmol) was dissolved in 100 mL of anhydrous pyridine under argon and cooled to -4° C. To this solution maintained at approximately 0° C. was added dropwise 11.3 g (59.22 mmol) of p-toluenesulfonyl chloride dissolved in 100 mL of pyridine. Following addition, the mixture was placed in the refrigerator (0°-4° C.) overnight. Water (150 mL) was added, and the aqueous mixture extracted with 4×200 mL of ether. The ether layers were combined, washed with 3×150 mL of water, 3×150 mL of saturated copper sulfate solution (until no dark blue color remained), 2×100 mL of water, 3×150 mL of brine, dried (Na2SO4), filtered, and evaporated under reduced pressure. The crude rosylate was purified by column chromatography using ethyl acetate:hexanes (1:1) to provide the title compound, 16.7 g (95%) as white solid: mp 48°-49° C.; [α]D25 -3.7°(C=0.3, CH3OH); IR (Kbr, cm-1) 2989, 1785, 1390, 1357, 1278; 1H NMR (CDCl3) δ 7.80 (d, J=8.3 Hz, 2H), 7.36 (d, J=8.3 Hz, 2H), 4.43 (dd, J=4.4, 8.1 Hz, 1H), 4.27-4.14 (m, 2H), 2.46 (s, 3H), 2.3-2.17 (m, 1H), 2.09-1.92 (m, 1H), 1.58 (s, 3H), 1.51 (s, 3H); HRMS calculated for C14H18O6S (M+), 314.0824, found 314.0817.

Workup

  1. temperatureTo this solution maintained at approximately 0° C.
  2. additionaddition
  3. customwas placed in the refrigerator (0°-4° C.) overnight
  4. extractionthe aqueous mixture extracted with 4×200 mL of ether
  5. washwashed with 3×150 mL of water, 3×150 mL of saturated copper sulfate solution (until no dark blue color
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude rosylate was purified by column chromatography

Sources & evidence

ORD record
ord-c3a65c02b1be4da3a39bf20c00e5a2fb
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

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