Water → Methyl 3-[4-[2-(phenoxazin-10-yl)ethoxy]phenyl]-2-ethoxypropanoate

HRID 495703Notes

Reaction equation

CS([O:5][CH2:6][CH2:7][N:8]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[O:15][C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)(=O)=O.O[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([O:35][CH2:36][CH3:37])[C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:20]1[C:21]2[N:8]([CH2:7][CH2:6][O:5][C:23]3[CH:24]=[CH:25][C:26]([CH2:29][CH:30]([O:35][CH2:36][CH3:37])[C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:28]=3)[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[O:15][C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(phenoxazin-10-yl)ethyl methanesulfonate (1.75 g, 5.0 mmol), methyl 3-(4-hydroxyphenyl)-2-ethoxypropanoate (1.5 g, 0.68 mmol) and potassium carbonate (3.16 g) in dry dimethylformamide (20 mL) was stirred for 12 h at 80° C. The reaction mixture was cooled to room temperature (ca. 25° C.). Water (30 mL) was added and extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with water (50 mL), dried (Na2SO4) and evaporated. The residue was chromatographed using a mixture of ethyl acetate and pet. ether (1:9) to afford the title compound (1.15 g, 47%) as a white solid. mp 89-90° C. 1H NMR data matches with the desired product (see above).

Workup

temperatureThe reaction mixture was cooled to room temperature (ca. 25° C.)
extractionextracted with ethyl acetate (2×50 mL)
washThe combined organic extracts were washed with water (50 mL)
dry with materialdried (Na2SO4)
customevaporated
customThe residue was chromatographed
additiona mixture of ethyl acetate and pet. ether (1:9)

Sources & evidence

ORD record: ord-d5bfc8d7fc5b4b3383f3f72465e30523
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939988B1

Reaction notes

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