Diethylamine → N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)amine

HRID 1778333Notes

Reaction equation

HRID 1778333 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].Br[CH2:7]/[CH:8]=[CH:9]\[Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14]>C1COCC1>[CH2:1]([N:3]([CH2:4][CH3:5])[CH2:7]/[CH:8]=[CH:9]\[Sn:10]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 10949620[(Z)-3-bromoprop-1-enyl]-tributylstannane2×

Product 1

HCID 86684726N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylamine (19 mL) was added to a solution of ((Z)-3-bromoprop-1-enyl)-tributyl-stannane (Intermediate 2, 7.52 g) in THF (60 mL) and the mixture was stirred for 3 hours. The reaction mixture was evaporated to dryness and the residue was purified by chromatography on a silica column which had been pre-washed with 20% triethylamine in acetonitrile. The column was eluted with a mixture of ethyl acetate and pentane with a gradient of 0-10% to give N,N-diethyl-N-((Z)-1-tributylstannanylprop-1-en-3-yl)-amine (4.75 g) as an orange oil.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue was purified by chromatography on a silica column which
  3. washhad been pre-washed with 20% triethylamine in acetonitrile
  4. washThe column was eluted with a mixture of ethyl acetate and pentane with a gradient of 0-10%

Sources & evidence

ORD record
ord-954e0a25bfea4940a99b6e93564bdd6f
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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