Potassium Carbonate → (E)-3-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester

HRID 19380

Reaction equation

[OH:1][C:2]([CH3:12])([CH3:11])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=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:7]1[CH:8]=[CH:9][C:4]([CH2:3][C:2]([OH:1])([CH3:12])[CH3:11])=[CH:5][CH:6]=1)\[CH3:19])[CH3:14]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred mixture of 4-(2-hydroxy-2-methyl-propyl)-phenol (0.850 g, 5.11 mmol) and ethyl-2-butynoate (3.45 g, 30.66 mmol) in tetrahydrofuran (20 mL) was added potassium carbonate (0.710 g, 5.11 mmol). The mixture was heated in a sealed tube at 80° C. for 5.5 h. The reaction mixture was then cooled to room temperature. The solids were isolated by filtration and washed with a small amount of tetrahydrofuran. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which afforded (E)-3-[4-(2-hydroxy-2-methyl-propyl)-phenoxy]-but-2-enoic acid ethyl ester (1.16 g, 81%) as a viscous colorless oil.

Workup

temperatureThe reaction mixture was then cooled to room temperature
customThe solids were isolated by filtration
washwashed with a small amount of tetrahydrofuran
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by flash chromatography (silica gel, 0% to 30% ethyl acetate/hexanes) which

Sources & evidence

ORD record: ord-0f41052e47d44f0ca617334a7c262752
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Linked notes

Loading…