Tetrabutylammonium Fluoride → HCID 53429202, compound

HRID 561822Notes

Reaction equation

HRID 561822 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:16]=1)[CH:12]=[O:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:16]=1)[CH:12]=[O:13]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866359203-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzaldehyde

Product 1

HCID 53429202HCID 53429202, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[tert-butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzaldehyde from the previous step (1 eq.) in THF (0.2 M) was added tetrabutylammonium fluoride (1.0 M THF solution, 1.1 eq.). The resulting reaction mixture was then stirred at RT for 30 min. The reaction was quenched sat. aq. NH4Cl and then extracted with ether. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. Further purification of the crude product thus obtained by way of column chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc) afforded the title compound as a pale yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched sat. aq. NH4Cl
  3. extractionextracted with ether
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customFurther purification of the crude product
  9. customthus obtained by way of column chromatography (SiO2, Hex→3:2 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-c64d786236e64ee9af11f37fe2412c9c
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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