Ammonium Chloride → HCID 67148527, compound

HRID 2428111Notes

Reaction equation

HRID 2428111 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([SiH2][O:24][C:25](C)(C)[C:26]1[CH:27]=[C:28]([CH2:33][CH2:34][NH:35][C:36](=[O:38])[CH3:37])[CH:29]=[CH:30][C:31]=1[Cl:32])(C)(C)C.[NH4+].[Cl-]>C1COCC1>[Cl:32][C:31]1[CH:30]=[CH:29][C:28]([CH2:33][CH2:34][NH:35][C:36](=[O:38])[CH3:37])=[CH:27][C:26]=1[CH2:25][OH:24]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 137329926HCID 137329926, compound

Product 1

HCID 67148527HCID 67148527, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 1.12 mL, 1.12 mmol) was added to a sol. of N-{2-[3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-phenyl]-ethyl}-acetamide (190 mg, 0.555 mmol) in THF (7.10 mL) at 0° C. The mixture was stirred for 1 h while warming up to rt. Aq. sat. NH4Cl was added, and the mixture was extracted with EtOAc (3×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC(CH2Cl2/MeOH 19:1) yielded the title compound (100 mg, 79%). LC-MS: tR=0.67 min; ES+: 284.11.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×)
  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 19:1)

Sources & evidence

ORD record
ord-d251d8efaa414c3abe4c4607acdaf872
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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