Benzoic Acid → HCID 12140308, compound

HRID 1476124Notes

Reaction equation

[F-].C([N+](C[CH2:16][CH2:17][CH3:18])(CCCC)CCCC)CCC.C(OC1(O[Si](C)(C)C)CC1)C.C1(P(=[CH:49][C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C1C=CC=CC=1>C1COCC1.C(OCC)C>[C:16]1(=[CH:49][C:50]([O:52][C:53]([CH3:54])([CH3:55])[CH3:56])=[O:51])[CH2:17][CH2:18]1

Participants

Conditions

Temperature: 80 °C

Procedure

At room temperature, 55 ml (55 mmol) of a 1 M solution of tetra-n-butylammonium fluoride in THF were added dropwise to a solution of 9.65 g (55.34 mmol) of [(1-ethoxycyclopropyl)oxy](trimethyl)silane, 25 g (66.41 mmol) of tert-butyl (triphenyl-λ5-phosphanylidene)-acetate and 8.11 g (66.41 mmol) of benzoic acid in 240 ml of THF. After 1 h of stirring, the reaction mixture was heated to 80° C. and stirred at this temperature for 2 h. Using a rotary evaporator, the solvent was then distilled off (200 mbar, bath temperature 40° C.). The residue obtained was taken up in diethyl ether and the mixture was cooled to 4° C. and allowed to stand at this temperature for 1 h. The resulting precipitate (triphenylphosphane oxide) was filtered off. Using a rotary evaporator, the filtrate was then freed from the solvent. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave 3.58 g (42% of theory) of the title compound.

Workup

stirringstirred at this temperature for 2 h
customa rotary evaporator
distillationthe solvent was then distilled off (200 mbar, bath temperature 40° C.)
customThe residue obtained
temperaturethe mixture was cooled to 4° C.
waitto stand at this temperature for 1 h
filtrationThe resulting precipitate (triphenylphosphane oxide) was filtered off
customa rotary evaporator

Sources & evidence

ORD record: ord-589912ff450b4ea3b8a97b5799674c21
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018414B2

Reaction notes

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