Tetrabutylammonium Fluoride → HCID 15538829, compound

HRID 1901405Notes

Reaction equation

HRID 1901405 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([C:15]([O:23][CH3:24])=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.CCCCCC>C1COCC1>[CH:20]([C:16]([CH:17]([CH3:19])[CH3:18])=[C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[CH:10]=1)[O:23][CH3:24])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 15389177HCID 15389177, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 15538829HCID 15538829, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.97 g (2.78 mmol) of alkene 1a in 30 ml of dry THF was added 0.81 g (1.1 eq.) of tetra-n-butylammonium fluoride. After stirring for one hour TLC (silica, 20% ethyl acetate/hexane) showed complete conversion of starting material to a new compound. The THF was evaporated and the residue dissolved in ethyl acetate. The ethyl acetate solution was extracted four times with water and dried. Silica gel (2 g) was added and the solvent evaporated. The material was purified by column chromatography on silica gel, eluting with 10-20% ethyl acetate/hexane yielding 0.568 g (87%) of 1b: 1H NMR (CDCl3) δ 7.5-6.5 (m, 4H), 4.91 (s, 1H), 3.20 (s, 3H), 2.47 (sept, 1H), 2.33 (sept, 1H), 1.25 (d, 6H), 0.92 (d, 6H); 13C NMR (CDCl3) δ 129.25, 124.98, 122.60, 116.54, 114.98, 114.56, 56.38, 30.52, 26.80, 22.11, 21.08; Mass spectrum (m/z): 234, 219, 191; exact mass, cald'd. 234.1620, found 234.1620.

Workup

  1. customThe THF was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate
  3. extractionThe ethyl acetate solution was extracted four times with water
  4. customdried
  5. additionSilica gel (2 g) was added
  6. customthe solvent evaporated
  7. customThe material was purified by column chromatography on silica gel
  8. washeluting with 10-20% ethyl acetate/hexane yielding 0.568 g (87%) of 1b

Sources & evidence

ORD record
ord-496e99f8598b458892793a113713a198
Source dataset
uspto-grants-1996_11
Patent number
US05578253

Reaction notes

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