Water → 2-Dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthalene

HRID 741778Notes

Reaction equation

HRID 741778 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][CH:14]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH2:13][CH2:12]2.[CH3:24][Sn:25](Cl)([CH3:27])[CH3:26].O>C1COCC1>[CH2:18]([N:17]([CH2:21][CH2:22][CH3:23])[CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[C:7]([Sn:25]([CH3:27])([CH3:26])[CH3:24])[CH:8]=[CH:9][CH:10]=2)[CH2:15]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Product 1

HCID 194270892-Dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthaleneYield 152.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Butyllithium (1.2M in hexane; 2.8 ml; 3.4 mmol) was added to a solution of 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene (1 g; 3.22 mmol) in THF (50 ml) at -78° C. After 1.5 hr., a solution of trimethyltin chloride (1.3 g, 2.0 mmol) in THF (20 ml) was added. The reaction mixture was allowed to warm to room temperature, stirred overnight at room temperature, poured into water, and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product. Purification by chromatography using 1:10 methanol:methylene chloride gave 1.2 g of the desired product which was used directly in the next step.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by chromatography

Sources & evidence

ORD record
ord-8b933f1eaa9641e48dc6a9b94fecf6a2
Source dataset
uspto-grants-1996_09
Patent number
US05552444

Reaction notes

Loading…