反応 #1702066

ord-2b8a0550c0384e25b553d30943f03be0

反応方程式

CC1(C)CCC(C)(C)c2cc(O)ccc21
5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene
CC(C)(C)C(=O)Cl
pivaloyl chloride
CC(C)(C)C(=O)c1cc2c(cc1O)C(C)(C)CCC2(C)C
5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl tert-butyl ketone

反応条件

温度
120°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    洗浄the organic layer was washed by water
  2. 2
    乾燥a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
  3. 3
    濃縮concentrated under reduced pressure
  4. 4
    その他The crude product was purified by silica gel chromatography

実験手順

The synthesis process is as set forth in the chemical reaction formula below. The TiCl4 in the reaction path stands for titanium chloride. To 5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene (409 mg, 2.00 mmol) were added titanium chloride (417 mg, 2.20 mmol) and pivaloyl chloride (361 mg, 2.99 mmol) followed by stirring at 120° C. for 1 hour. The reaction solution was diluted by dichloromethane, and the organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (40/3) as an elution solvent. The yield was 53.6 mg (9.0%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08765719B2uspto-grants-2014_07