Water → methyl [2-[1-(((2R)-oxiranyl)methoxy)ethyl]phenyl]propynoate

HRID 1181605Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][CH2:11][C@H:12]1[CH2:14][O:13]1)[CH3:9].[C:15]([O:19][CH3:20])(=[O:18])[C:16]#[CH:17].C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[O:13]1[CH2:14][C@@H:12]1[CH2:11][O:10][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:17]#[C:16][C:15]([O:19][CH3:20])=[O:18])[CH3:9]

Participants

Conditions

Temperature: 65 °C

Procedure

(R)-2-[[1-(2-Iodophenyl)ethoxy]methyl]oxirane (1.50 g) obtained in Step 1 was dissolved in tetrahydrofuran (15 ml), methyl propynoate (1.66 g), tetrakis(triphenylphosphine)palladium(0) (69.2 mg), copper iodide (37.5 mg) and potassium carbonate (2.72 g) were successively added, and the mixture was stirred overnight at 65° C. The reaction mixture was cooled to room temperature, water was added and, after filtration through celite, the filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the title compound (43 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationafter filtration through celite
extractionthe filtrate was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-3795be1c7c054032b725170242f04d67
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07285572B2

Reaction notes

Loading…