Potassium Carbonate → (1S,2R)-3-(benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol

HRID 1506989Notes

Reaction equation

C([O:4][C@H:5]([CH2:15][O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[OH:7])(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[CH2:17]([O:16][CH2:15][C@@H:5]([OH:4])[C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Cl:14])[OH:7])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (1S,2R)-3-(benzyloxy)-1-(2-chlorophenyl)-1-hydroxypropan-2-yl acetate (Preparation example 374, 1.2 g, 3.58 mmole) in MeOH (16.2 mL) and H2O (1.8 mL) was added K2CO3 (1.48 g, 10.74 mmole) at 0° C. The mixture was stirred for 1.5 hr at 0° C. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (1.0 g, 94%).

Workup

customconsumption of SM
customThe reaction mixture was quenched with H2O at 0° C.
extractionthen extracted with EtOAc
extractionThe aqueous layer was extracted with EtOAc
customseparated
washThe combined organic layer was washed with H2O
dry with materialdried over MgSO4
customevaporated under reduced pressure
customThe crude compound was purified by silica ge column

Sources & evidence

ORD record: ord-29b9d86c3a844c5f8aeeb93cc6069b0f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221783B2

Reaction notes

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