Water → HCID 20661170, compound

HRID 1066686Notes

Reaction equation

HRID 1066686 reaction equation
[OH-].[K+].[C:3]1([CH3:13])[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[O:14]1[C@H:18]([CH2:19][CH2:20][CH3:21])[C@H:15]1[CH2:16][OH:17].O>C(OCC)C>[C:3]1([CH3:13])[CH:8]=[CH:7][C:6]([S:9]([O:17][CH2:16][C@H:15]2[O:14][C@@H:18]2[CH2:19][CH2:20][CH3:21])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 11073386(2R,3R)-(+)-3-PROPYLOXIRANEMETHANOL, 97% (94% EE/GLC)

Product 1

HCID 20661170HCID 20661170, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

26 g of powdered potassium hydroxide (0.45 mol) and 14.3 g (75 mmol) of p-toluenesulfonyl chloride were added in succession at −10° C. to a stirred solution of (2R,3R)-2,3-epoxy-1-hexanol (8 g, 69 mmol) in diethyl ether. After 5 hours at 0° C., the reaction mixture was poured into 200 ml of water. The organic layer was separated off and the aqueous phase was extracted twice with 100 ml of diethyl ether in each case. The combined organic phases were washed with concentrated sodium chloride solution and dried over anhydrous sodium sulfate. After removing the solvent, (2-R,3R)-2,3-epoxyhexyl p-toluenesulfonate remained in the form of light yellow crystals which crystallized from diethyl ether/n-hexane as colorless needles (yield: 71%; [α]D20=+36.3°(c=2.0 in trichloromethane)).

Workup

  1. customThe organic layer was separated off
  2. extractionthe aqueous phase was extracted twice with 100 ml of diethyl ether in each case
  3. washThe combined organic phases were washed with concentrated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing the solvent, (2-R,3R)-2,3-epoxyhexyl p-toluenesulfonate
  6. customcrystallized from diethyl ether/n-hexane as colorless needles (yield: 71%; [α]D20=+36.3°(c=2.0 in trichloromethane))

Sources & evidence

ORD record
ord-1001d61273214c1193c0753a5bbe7bb5
Source dataset
uspto-grants-2001_06
Patent number
US06245328B1

Reaction notes

Loading…