Water → HCID 59921413, compound

HRID 1019360Notes

Reaction equation

HRID 1019360 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:15]([CH3:25])([O:20][Si](C)(C)C)[C:16]([F:19])([F:18])[F:17])=[C:7]([CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:15]([OH:20])([CH3:25])[C:16]([F:18])([F:19])[F:17])=[C:7]([CH2:9][CH2:10][O:11][C:12](=[O:14])[CH3:13])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59921412HCID 59921412, compound

Product 1

HCID 59921413HCID 59921413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the crude reaction mixture described in example 2 containing a solution of acetic acid 2-[5-methoxy-2-(2,2,2-trifluoro-1-methyl-1-trimethylsilanyloxy-ethyl)-phenyl]-ethyl ester was added tetrabutylammonium fluoride (52.9 mL of a 1.0M solution in tetrahydrofuran, 52.9 mmol). The reaction mixture was stirred one hour after which GC/MS and HPLC analysis showed no starting material. For characterization purposes, the reaction mixture was poured into water and extracted with methyl tert-butyl ether (75 mL). The organic layer was washed with water (75 mL) and brine (50 mL), dried over magnesium sulfate, filtered and concentrated to provide a crude oil. 1H NMR (400 MHz, CDCl3) δ1.82 (s, 3), 2.01 (s, 3), 2.98-3.06 (m, 2), 3.55 (dt, 1, J=13.7, 6.8), 3.79 (s, 3), 4.27-4.34 (m, 2), 6.73-6.77 (m, 2), 7.28 (d, 1, J=8.5). 13C NMR (100 MHz, CDCl3) δ20.92, 25.50, 34.16, 55.10, 66.49, 76.67 (q, J=30.3), 111.55, 118.25, 126.02 (q, J=286), 128.67, 129.56, 139.70, 159.20, 171.32. IR 3453, 1720, 1610, 1249, 1161, 1134, 1038 cm−1. Analysis calculated for C14H17F3O4: C, 54.90; H, 5.59. Found: C, 55.03; H, 5.85.

Workup

  1. customTo the crude reaction mixture
  2. extractionextracted with methyl tert-butyl ether (75 mL)
  3. washThe organic layer was washed with water (75 mL) and brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide a crude oil

Sources & evidence

ORD record
ord-e278e1055a5343b8b7abad8419ac5931
Source dataset
uspto-grants-2002_11
Patent number
US06486325B1

Reaction notes

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