Hexane → N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-(tributyl-stannyl)benzyl)-N-methylprop-2-en-1-amine

HRID 926930Notes

Reaction equation

HRID 926930 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=1I)[CH2:15][N:16]([CH3:20])[CH2:17][CH:18]=[CH2:19])([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5].C([Li])CCC.CCCCCC.[CH2:38]([Sn:42](Cl)([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:43][CH2:44][CH2:45][CH3:46])[CH2:39][CH2:40][CH3:41].[Cl-].[NH4+]>C1COCC1>[F:1][C:2]([F:26])([F:25])[C:3]([C:12]1[CH:13]=[C:14]([CH:21]=[CH:22][C:23]=1[Sn:42]([CH2:43][CH2:44][CH2:45][CH3:46])([CH2:47][CH2:48][CH2:49][CH3:50])[CH2:38][CH2:39][CH2:40][CH3:41])[CH2:15][N:16]([CH3:20])[CH2:17][CH:18]=[CH2:19])([O:8][CH2:9][O:10][CH3:11])[C:4]([F:7])([F:6])[F:5]

Participants

7

Reactant 5

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 87358512N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-iodo-benzyl)-N-methylprop-2-en-1-amineHCID 178418339Butyllithium

Product 1

HCID 87358460N-(3-(1,1,1,3,3,3-hexafluoro-2-(methoxymethoxy)propan-2-yl)-4-(tributyl-stannyl)benzyl)-N-methylprop-2-en-1-amineYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Compound 12 (470 mg, 945 μmol) was dissolved in freshly distilled THF (5 mL) under nitrogen atmosphere and cooled to −78° C. n-butyllithium 1.6M in hexane solution (886 μL, 1.42 mmol) was then added and the mixture stirred 30 min at −78° C. Tributyltin chloride (462 mg, 1.42 mmol) in solution in THF (2 mL) was added and the mixture let to warm to room temperature overnight. A 0.1M ammonium chloride solution (5 mL) was added to the reactionnal mixture. The organic layer was isolated and the aqueous layer was extracted with dichloromethane (2×5 mL). The organic layers were combined and dried over sodium sulfate. After solvent evaporation under reduced pressure, the residue was purified over silica gel with heptane/acetone (98/2) as eluant to give 524 mg (794 μmol, 84% yield) of a yellowish oil.

Workup

  1. additionwas then added
  2. temperatureto warm to room temperature overnight
  3. customThe organic layer was isolated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×5 mL)
  5. dry with materialdried over sodium sulfate
  6. customAfter solvent evaporation under reduced pressure
  7. customthe residue was purified over silica gel with heptane/acetone (98/2) as eluant

Sources & evidence

ORD record
ord-5804c69b872e475e964006c9031baf74
Source dataset
uspto-grants-2016_03
Patent number
US09290421B2

Reaction notes

Loading…