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

HRID 129930Notes

Reaction equation

HRID 129930 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-0f89195b860b4650ac558c089368650d
Source dataset
uspto-grants-1995_11
Patent number
US05470977

Reaction notes

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