Potassium Carbonate → (S)-1-(p-2-isopropoxyethoxymethylphenoxy)-2,3-epoxypropane

HRID 2288260Notes

Reaction equation

[CH:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:3])[CH3:2].[F-].[Cs+].C(=O)([O-])[O-].[K+].[K+].[N+](C1C=C(S(O[CH2:37][C@H:38]2[O:40][CH2:39]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C.O>[CH:1]([O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:37][C@H:38]2[O:40][CH2:39]2)=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

p-(2-Isopropoxyethoxy)methylphenol (5 g) was dissolved in DMF (30 ml) under nitrogen atmosphere and the solution was cooled to 0° C. Cesium fluoride (0.72 g) and potassium carbonate (4.27 g) were added thereto, and the mixture was stirred for 1 hour. Then (S)-glycidyl m-nitrobenzenesulfonate (6.16 g, 99.7% e.e.) was added thereto and the mixture was stirred for 24 hours at the same temperature. After the reaction, water was added to the filtrate, the solution was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, condensed and the residue was subjected to silica gel chromatography (hexane/ethyl acetate; 1:1) to give 6.08 g of (S)-1-(p-2-isopropoxyethoxymethylphenoxy)-2,3-epoxypropane (yield 96%, optical purity 99.6% e.e.) as a colorless oil.

Workup

stirringthe mixture was stirred for 24 hours at the same temperature
additionwas added to the filtrate
extractionthe solution was extracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate, condensed

Sources & evidence

ORD record: ord-7318814ed964412b8fcab9e74ef7d2b0
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087512

Reaction notes

Loading…