Hydrochloric Acid → HCID 59327161, compound

HRID 1880175Notes

Reaction equation

HRID 1880175 reaction equation
[F:1][C:2]([Si](C)(C)C)([F:4])[F:3].[F-:9].C([N+:14]([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:19][CH2:20][CH2:21]C)CCCC)CCC.[CH2:27]1[CH2:31][O:30]CC1.Cl.[CH3:33]COC(C)=O>>[F:9][C:23]1[C:24]([C:25]2[CH2:26][CH2:27][C:31]([C:2]([F:4])([F:3])[F:1])([OH:30])[CH:33]=2)=[CH:21][CH:20]=[CH:19][N:14]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 59327161HCID 59327161, compound

Procedure

After 2 h, more (trifluoromethyl)trimethylsilane (1.906 g, 13.40 mmol) and tetra-n-butylammonium fluoride, 1.0M in THF (0.536 mL, 0.536 mmol) were added. After a total of 4 h, 10% hydrochloric acid solution (50 ml) was added, and the reaction was stirred for 15 min. The solution was diluted with EtOAc (200 ml) and washed with 10% hydrochloric acid solution (50 ml), water (50 ml) and brine (50 ml), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluant: 10-45% EtOAc/hexane), affording the product as a yellow oil. MS (ESI, pos. ion) m/z: 248.0 (M+1).

Workup

  1. washwashed with 10% hydrochloric acid solution (50 ml), water (50 ml) and brine (50 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography (eluant: 10-45% EtOAc/hexane)

Sources & evidence

ORD record
ord-3a6080a1c1604a8f80be0acf463799ac
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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