Ethanol → Ethyl 3-(3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl)-3-cyclopropylpropanoate

HRID 1049407Notes

Reaction equation

[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:26]([CH:37]2[CH2:39][CH2:38]2)[CH:27]2C(=O)O[C:30](C)([CH3:34])[O:29][C:28]2=[O:36])[CH:23]=[CH:24][CH:25]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>CN(C=O)C>[Si:1]([O:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:26]([CH:37]2[CH2:38][CH2:39]2)[CH2:27][C:28]([O:29][CH2:30][CH3:34])=[O:36])[CH:23]=[CH:24][CH:25]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-((3-(((tert-butyldiphenylsilyl)oxy)methyl)phenyl) (cyclopropyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione (5.07 g) in DMF (40 mL) was added ethanol (20 mL), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with ethyl acetate, and the extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.55 g) as a pale-yellow oil.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, and water
additionwas added to the residue
extractionThe mixture was extracted with ethyl acetate
washthe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-dcd09b246ea94bc9af92bd9a9f90ce9e
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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