Ethyl Acetate → HCID 67148459, compound

HRID 2428099Notes

Reaction equation

HRID 2428099 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([SiH2][O:24][C:25](C)(C)[C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][C:36]=1[Cl:37])[CH2:29][NH:30][C:31](=[O:33])[CH3:32])(C)(C)C.CCOC(C)=O>C1COCC1>[Cl:37][C:36]1[CH:35]=[CH:34][C:28]([CH2:29][NH:30][C:31](=[O:33])[CH3:32])=[CH:27][C:26]=1[CH2:25][OH:24]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 137329922HCID 137329922, compound

Product 1

HCID 67148459HCID 67148459, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 12.0 mL, 12.0 mmol) was added to a sol. of N-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzyl]-acetamide (2.05 g, 6.00 mmol) in THF (60 mL) at 0° C. The mixture was stirred for 2 h while warming up to rt. EtOAc (100 mL) was added, and the mixture was washed with aq. sat. NH4Cl (1×) 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(CH2Cl2/MeOH 90:10) yielded the title compound (750 mg, 59%). LC-MS: tR=0.63 min; ES+: 237.09.

Workup

  1. washthe mixture was washed with aq. sat. NH4Cl (1×) 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(CH2Cl2/MeOH 90:10)

Sources & evidence

ORD record
ord-16dcae3f1fd84bc59c0e3d456193f207
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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