Tetrahydrofuran → HCID 66931047, compound

HRID 511985Notes

Reaction equation

HRID 511985 reaction equation
COC([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=O.[F:25][C:26]([Si](C)(C)C)([F:28])[F:27].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C[O:54][CH2:53]C1>C1(C)C=CC=CC=1.Cl>[F:25][C:26]([F:28])([F:27])[C:53]([C:13]1([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:14]=[CH:15][CH:16]=[C:11]([C:7]2[CH:6]=[CH:5][CH:10]=[CH:9][CH:8]=2)[CH2:12]1)=[O:54]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 20099919HCID 20099919, compound

Product 1

HCID 66931047HCID 66931047, compoundYield 940.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 29 (0.1 g, 0.314 mmol) in anhydrous toluene (5 mL) was cooled to −78° C., under nitrogen, and trifluoromethyltrimethylsilane (62.5 mg, 0.44 mmol) was added. The mixture was stirred for 15 min at −78° C., then a 1M anhydrous solution of tetrabutylammonium fluoride in THF (0.026 ml, 0.026 mmol) was added and the resultant mixture was gradually warmed to room temperature. After stirring for 12 h at room temperature, the reaction mixture was diluted with 4N HCl solution (2 mL) and stirred for an additional 2 h period. The organic layer was separated and the aqueous layer was extracted with diethyl ether (20 mL). The combined organic layer was washed with aqueous saturated NaHCO3 solution (5 mL) and brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (25% diethyl ether-hexane) and the fraction that contains the product 30 and its hydrate form (2:1 ratio by 1H NMR) was concentrated and dried in high vacuum (in the presence of P2O5) to give pure compound 30 (0.0876 g, 76% yield) as a viscous liquid.

Workup

  1. stirringAfter stirring for 12 h at room temperature
  2. stirringstirred for an additional 2 h period
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with diethyl ether (20 mL)
  5. washThe combined organic layer was washed with aqueous saturated NaHCO3 solution (5 mL) and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel (25% diethyl ether-hexane)
  9. concentrationwas concentrated
  10. dry with materialdried in high vacuum (in the presence of P2O5)

Sources & evidence

ORD record
ord-2175e96ea8644e398ba86bc37c92b611
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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