Borane;tetrahydrofuran → HCID 86602507, compound

HRID 854484Notes

Reaction equation

HRID 854484 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:17][Si:18]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:19][CH3:20])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:25][C:26](=O)[CH3:27].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:17][Si:18]([CH2:19][CH3:20])([CH2:21][CH3:22])[CH2:23][CH3:24])([C:13]([F:14])([F:15])[F:16])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[NH:25][CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 86602508HCID 86602508, compound

Product 1

HCID 86602507HCID 86602507, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.54 g (3.42 mmol) of crude N-[2-chloro-4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-acetamide in 20 mL of THF was treated with 6.85 mL of a 1M solution of BH3THF-complex in THF. The mixture was kept at reflux for 3 hours and the solvent evaporated. The residue was distributed between a saturated aqueous solution of NH4Cl and Et2O. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. Column chromatography on silica gel with n-heptane/EtOAc 95:5 yielded 0.922 g (61%) of [2-chloro-4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-phenyl]-N-ethyl-amine, colorless liquid, MS: 436 (MH+, 1Cl).

Workup

  1. temperatureat reflux for 3 hours
  2. customthe solvent evaporated
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c2c73dca79d342858d1723892bfd0378
Source dataset
uspto-grants-2007_08
Patent number
US07259178B2

Reaction notes

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