Potassium Carbonate → (E)-3-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-but-2-enoic acid ethyl ester

HRID 19398Notes

Reaction equation

[CH3:1][C:2]1([CH3:15])[O:6][C@@H:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:4][O:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([O:24][C:25](=[O:29])[C:26]#[C:27][CH3:28])[CH3:23]>CN(C)C1C=CN=CC=1.O1CCCC1>[CH2:22]([O:24][C:25](=[O:29])/[CH:26]=[C:27](/[O:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C@H:5]2[CH2:4][O:3][C:2]([CH3:15])([CH3:1])[O:6]2)=[CH:9][CH:10]=1)\[CH3:28])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenol (0.696 g, 3.34 mol), potassium carbonate (0.463 g, 0.003 mol), ethyl-2-butynoate (2.25 g, 0.020 mol) and a catalytic amount of 4-dimethylaminopyridine in tetrahydrofuran (15 mL) was placed in a sealed tube and heated at 80° C. for 6 h. The reaction mixture was cooled, filtered and the isolated solids washed with tetrahydrofuran. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which afforded (E)-3-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-phenoxy]-but-2-enoic acid ethyl ester (0.440 g, 41%) as a colorless oil.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered
washthe isolated solids washed with tetrahydrofuran
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which

Sources & evidence

ORD record: ord-001925c05344414d945b079d98bac1e9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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