Hydrochloric Acid → HCID 59511839, compound

HRID 1157942Notes

Reaction equation

[F:1][C:2]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:3]=1[O:4][Si:5]([CH:12]([CH3:14])[CH3:13])([CH:9]([CH3:11])[CH3:10])[CH:6]([CH3:8])[CH3:7].CN(CCN(CCN(C)C)C)C.C([Li])CCC.[CH:38](N1CCOCC1)=[O:39].Cl>C1COCC1>[F:1][C:2]1[C:3]([O:4][Si:5]([CH:6]([CH3:7])[CH3:8])([CH:12]([CH3:13])[CH3:14])[CH:9]([CH3:11])[CH3:10])=[CH:15][C:16]([O:19][CH3:20])=[CH:17][C:18]=1[CH:38]=[O:39]

Participants

Conditions

Temperature: -60 °C

Procedure

To a 240 ml THF solution containing 113 g of (2-fluoro-5-methoxyphenoxy)triisopropylsilane and 70 g of N,N,N′,N′,N″-pentamethyldiethylenetriamine there was added dropwise 150 ml of n-butyllithium (2.66 M, hexane solution) at −74° C., over a period of 50 minutes. After stirring at −60° C. for 3 hours, 70 ml of N-formylmorpholine was added. The temperature of the reaction mixture was slowly raised to 6° C. Next, 1N hydrochloric acid was added to the reaction mixture while cooling on ice, and then it was extracted with a mixture of hexane and t-butyl methyl ether and dried over anhydrous magnesium sulfate. The desiccant was filtered out and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (t-butyl methyl ether-heptane system) to obtain the target compound (113.26 g) as an oil.

Workup

temperatureThe temperature of the reaction mixture was slowly raised to 6° C
temperaturewhile cooling on ice
extractionit was extracted with a mixture of hexane and t-butyl methyl ether
dry with materialdried over anhydrous magnesium sulfate
filtrationThe desiccant was filtered out
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (t-butyl methyl ether-heptane system)

Sources & evidence

ORD record: ord-e0dc8eeb9a114dec9cf415a650d26107
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807690B2

Reaction notes

Loading…