Ethyl Acetate → N-(4-Chloro-3-hydroxymethyl-benzyl)-3,3,3-trifluoro-propionamide

HRID 2428103Notes

Reaction equation

HRID 2428103 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([SiH2][O:24][C:25](C)(C)[C:26]1[CH:27]=[C:28]([CH:38]=[CH:39][C:40]=1[Cl:41])[CH2:29][NH:30][C:31](=[O:37])[CH2:32][C:33]([F:36])([F:35])[F:34])(C)(C)C.CCOC(C)=O>C1COCC1>[Cl:41][C:40]1[CH:39]=[CH:38][C:28]([CH2:29][NH:30][C:31](=[O:37])[CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:27][C:26]=1[CH2:25][OH:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 137329921N-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-3,3,3-trifluoro-propionamide

Product 1

HCID 67148258N-(4-Chloro-3-hydroxymethyl-benzyl)-3,3,3-trifluoro-propionamideYield 65.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 9.10 mL, 9.10 mmol) was added to a sol. of N-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-3,3,3-trifluoro-propionamide (1.80 g, 4.55 mmol) in THF (45 mL) at 0° C. The mixture was stirred for 1 h while warming up to rt. EtOAc (100 mL) was added, and the mixture was washed with aq. sat. NH4Cl (3×) and water (4×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 70:30) yielded the title compound (835 mg, 65%). LC-MS: tR=0.76 min; ES+: 323.02.

Workup

  1. washthe mixture was washed with aq. sat. NH4Cl (3×) and water (4×)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (EtOAc/heptane 70:30)

Sources & evidence

ORD record
ord-f229817612d94f55942d92194cd24fd8
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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