Pivaloyl chloride → HCID 45270787, compound

HRID 1614884Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([CH3:13])([CH3:12])[CH2:7][CH2:6][C:5]([CH3:15])([CH3:14])[C:4]=2[CH:3]=1.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>Cl[Ti](Cl)(Cl)Cl.ClCCl>[C:17]([C:16]([C:11]1[C:2]([OH:1])=[CH:3][C:4]2[C:5]([CH3:15])([CH3:14])[CH2:6][CH2:7][C:8]([CH3:13])([CH3:12])[C:9]=2[CH:10]=1)=[O:21])([CH3:20])([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

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%).

Workup

washthe organic layer was washed by water
dry with materiala saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-2b8a0550c0384e25b553d30943f03be0
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765719B2

Reaction notes

Loading…