Tetrabutylammonium Fluoride → N-[4-Chloro-3-(hydroxymethyl)benzyl]-N-methylacetamide

HRID 561790Notes

Reaction equation

HRID 561790 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:13][N:14]([CH3:18])[C:15](=[O:17])[CH3:16])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:22][C:21]1[CH:20]=[CH:19][C:12]([CH2:13][N:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66761148N-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzyl]-N-methylacetamide

Product 1

HCID 66761682N-[4-Chloro-3-(hydroxymethyl)benzyl]-N-methylacetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzyl]-N-methylacetamide from the previous step (1 eq.) in THF (0.8M) was added tetrabutylammonium fluoride (1.0 M THF solution, 1.5 eq.). The resulting reaction mixture was stirred at RT for 1 h. After quenching the reaction with 10% aq. HCl, the mixture was extracted with EtOAc. The combined organic extracts were washed with sat. aq. NaHCO3 and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded a pale yellow oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) CH2Cl2:MeOH) afforded the title compound as a light yellow oil.

Workup

  1. customThe resulting reaction mixture
  2. customAfter quenching
  3. customthe reaction with 10% aq. HCl
  4. extractionthe mixture was extracted with EtOAc
  5. washThe combined organic extracts were washed with sat. aq. NaHCO3 and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customConcentration of the filtrate in vacuo afforded a pale yellow oil
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-8afb55e948fc4d53b99ed01e10bac271
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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