Triethylamine → 3-(2,4-Dihydroxyphenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester

To a solution of 3-amino-1-(2,6,6-trimethyl-cyclohex-3-enyl)-butan-1-one (2.38, 11.3 mmol, 10) and triethylamine (2.30 g, 22.6 mmol) in anhydrous THF (150 mL) stirred for 5 min at 22° C. is added 3-(2,4-dihydroxyphenyl)-acrylic acid (2.04 g, 11.3 mmol). To this heterogeneous solution is added BOP Reagent (5.00 g, 11.3 mmol; Aldrich #22,608-4) in DMF (10 mL), and the subsequent homogeneous reaction mixture is stirred for 1 h. The reaction mixture is partitioned between ether (200 mL) and water (400 mL); the organic layer is removed and washed with ether (200 mL). The combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL). The organic layer is dried over anhydrous magnesium sulfate, vacuum filtered and concentrated to give 3-(2,4-dihydroxy-phenyl)-acrylic acid 1,5-dimethyl-1-vinyl-hex-4-enyl ester as an oil that is purified by flash chromatography to give 11 as a colorless solid.

1. customThe reaction mixture is partitioned between ether (200 mL) and water (400 mL)
2. customthe organic layer is removed
3. washwashed with ether (200 mL)
4. washThe combined organic layers are washed sequentially with saturated sodium bicarbonate solution (200 mL) and brine (200 mL)
5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate, vacuum
6. filtrationfiltered
7. concentrationconcentrated

ORDレコード

ord-f5844642a03442089b5075c8e9f868d9

出典データセット

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07368415B2