Hydrochloric Acid → HCID 69682206, compound

HRID 394921Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[C:5](=[O:20])[C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:17])([CH3:16])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=2[CH:7]=1)[CH3:2].[CH2:22](O[Si](C)(C)C)[CH2:23][CH2:24][CH3:25].O([Si](C)(C)C)S(C(F)(F)F)(=O)=O.C([SiH](CC)CC)C.Cl>C(Cl)Cl.O>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([O:20][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]1[CH:15]=[CH:14][C:13]2[C:12]([CH3:16])([CH3:17])[CH2:11][CH2:10][C:9]([CH3:19])([CH3:18])[C:8]=2[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

6 g of oxo-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester and 2.6 g of butoxytrimethylsilane were dissolved in 200 ml of methylene chloride. The solution was cooled to 0° C., treated with 400 mg of trimethylsilyl triflate and stirred at 0° C. for 1.5 hours. After the dropwise addition of 2 g of triethylsilane, the reaction mixture was stirred at room temperature for 26 hours, then diluted with 500 ml of water, acidified with 2N hydrochloric acid and extracted with ether. The organic phase was washed with water, dried (Na2SO4) and the solvent evaporated. The oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane) to give 3.5 g of the title product as colorless oil.

Workup

stirringthe reaction mixture was stirred at room temperature for 26 hours
extractionextracted with ether
washThe organic phase was washed with water
dry with materialdried (Na2SO4)
customthe solvent evaporated
customThe oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane)

Sources & evidence

ORD record: ord-eefd3b6428104b38931fccb5974de1ea
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06603012B2

Reaction notes

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