Potassium Carbonate → (E)-3-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester

HRID 19373Notes

Reaction equation

[OH:1][C:2]([CH3:12])([CH3:11])[CH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:13]([O:15][C:16](=[O:20])[C:17]#[C:18][CH3:19])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:13]([O:15][C:16](=[O:20])/[CH:17]=[C:18](/[O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][C:2]([OH:1])([CH3:12])[CH3:11])[CH:5]=1)\[CH3:19])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-(2-hydroxy-2-methyl-propyl)-phenol (1.00 g, 6.01 mmol), ethyl-2-butynoate (4.00 g, 36.06 mol) and potassium carbonate (0.830 g, 6.01 mmol) in tetrahydrofuran (20 mL) in a sealed tube was heated to 80° C. for 3.75 h. The reaction mixture was then cooled and filtered. The solids were washed with a small amount of tetrahydrofuran and the combined filtrate was collected and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) to afford (E)-3-[3-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester (1.41 g, 84%) as a colorless oil.

Workup

temperatureThe reaction mixture was then cooled
filtrationfiltered
washThe solids were washed with a small amount of tetrahydrofuran
customthe combined filtrate was collected
concentrationconcentrated in vacuo
customThe residue was purified by flash column chromatography (silica gel, 0% to 30% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-89ac4a99ad0244b8b9ed4c6b0f4621e1
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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