Propylene Oxide → HCID 86720727, compound

HRID 520736Notes

Reaction equation

HRID 520736 reaction equation
[CH:1]1([S:4]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([Li])CCC.[O:17]1[CH:19]([CH3:20])[CH2:18]1.B(F)(F)F.CCOCC>C1COCC1>[OH:17][CH:19]([CH3:20])[CH2:18][C:1]1([S:4]([O:7][CH2:8][CH2:9][CH2:10][CH3:11])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6378Propylene OxideHCID 8000Boron trifluoride etherateHCID 10464888Butyl cyclopropanesulfonateHCID 178418339Butyllithium

Product 1

HCID 86720727HCID 86720727, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of butyl cyclopropanesulfonate 2 (1.2 g, 6.7 mmol) in THF (24 mL) was cooled to −78° C. and n-butyllithium (1.6M in n-hexane, 5.0 mL, 8.1 mmol) was added within 5 min. The mixture was stirred for 30 min and epoxypropane derivative 1 or 8 (8.1 mmol) was added followed by addition of boron trifluoride diethyl etherate (0.84 mL, 6.7 mmol). The solution was stirred for 1 h at −78° C., the cooling bath was removed and stirring was continued for 2 additional hours. For aqueous work-up diluted hydrochloric acid (10%, 0.8 mL), water (10 mL) and ethyl acetate (20 mL) were added. The organic layer was is concentrated at 40° C. to afford the corresponding butyl 1-[2-hydroxypropyl]cyclopropanesulfonate 3.

Workup

  1. stirringThe solution was stirred for 1 h at −78° C.
  2. customthe cooling bath was removed
  3. stirringstirring
  4. additionFor aqueous work-up diluted hydrochloric acid (10%, 0.8 mL), water (10 mL) and ethyl acetate (20 mL) were added
  5. concentrationThe organic layer was is concentrated at 40° C.

Sources & evidence

ORD record
ord-e0e139131b4f49a5a01878abc898c9f1
Source dataset
uspto-grants-2016_05
Patent number
US09328066B2

Reaction notes

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