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

HRID 67285Notes

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-ff983c8af8fc44d2ba12c9cc4c0f9fc1
Source dataset: uspto-grants-1982_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04346042

Reaction notes

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