Hydrochloric Acid → (R)-3-mesyloxy-2-hydroxy-1-chloropropane

HRID 280368Notes

Reaction equation

[S:1]([O:5][CH2:6][C@H:7]1[O:9][CH2:8]1)([CH3:4])(=[O:3])=[O:2].[ClH:10]>>[S:1]([O:5][CH2:6][C@@H:7]([OH:9])[CH2:8][Cl:10])([CH3:4])(=[O:3])=[O:2]

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 12461090(S)-glycidyl methanesulfonate

Product 1

HCID 12461093(R)-3-mesyloxy-2-hydroxy-1-chloropropaneYield 85%

Procedure

Concentrated HCl (20 ml) was added to (S)-3-mesyloxy-1,2-epoxypropane (5.0 g, 0.033 m) over 15-20 minutes. After stirring for an additional 30 minutes, the water was removed through the addition and subsequent evaporation of ethanol. Finally, residual ethanol was removed at room temperature and 0.1 mm to give (R)-3-mesyloxy-2-hydroxy-1-chloropropane, (5.4 g, 85%); 1H NMR (CDCl3) 4.35 (2H, d), 4.1 (1H, m), 3.65 (2H, d), 3.1 (3H, s), 2.9 (1H, broad s); [α]D22 =7.1° (c=5.78, CH3OH).

Workup

customthe water was removed through the addition and subsequent evaporation of ethanol
customFinally, residual ethanol was removed at room temperature

Sources & evidence

ORD record: ord-18a3ea360f5544b98ef633197ddcccf4
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04588824

Reaction notes

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