Lithium diisopropylamide → HCID 85749769, compound

HRID 1872291Notes

Reaction equation

HRID 1872291 reaction equation
[CH2:1]([Sn:5]1([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][CH:9]=[CH:8][CH:7]=[C:6]1[Li])[CH2:2][CH2:3][CH3:4].C([Sn]1(CCCC)C=CCC=C1)CCC.C([N-]C(C)C)(C)C.[Li+].[CH2:38]([Sn:42]1([CH2:51][CH2:52][CH2:53][CH3:54])[CH:47]=[CH:46][CH:45]([CH2:48][CH2:49]Br)[CH:44]=[CH:43]1)[CH2:39][CH2:40][CH3:41]>C1COCC1.O>[CH2:1]([Sn:5]1([CH2:12][CH2:13][CH2:14][CH3:15])[CH:10]=[CH:9][CH:8]([CH2:49][CH2:48][CH:45]2[CH:44]=[CH:43][Sn:42]([CH2:51][CH2:52][CH2:53][CH3:54])([CH2:38][CH2:39][CH2:40][CH3:41])[CH:47]=[CH:46]2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 2724682Lithium diisopropylamideHCID 11347074Stannin, 1,1-dibutyl-1,4-dihydro-HCID 12842272HCID 12842272, compoundHCID 178506717HCID 178506717, compound

Product 1

HCID 85749769HCID 85749769, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1 ,1-dibutyl-1-stannacyclohexadienyllithium prepared from 1,1-dibutyl-1-stannacyclohexa-2,5-diene (0.08 g, 2.67 mmol) and 2.67 mmol of lithium diisopropylamide (LDA) in 20 mL of THF was added to a solution of 1,1 -dibutyl-4-(2-bromoethyl)-1-stannacyclohexa-2,5-diene (1.0 g, 2.46 mmol) in 5 mL THF at -78° C. After stirring approximately 16 hours, 10 mL of water were added and the product was extracted with pentane, dried over MgSO4, and evaporated to dryness. The red residue left contained 1.25 g (81 percent) of crude product.

Workup

  1. extractionthe product was extracted with pentane
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. waitThe red residue left

Sources & evidence

ORD record
ord-996280f8fe7e4bf19f89fbeb35512660
Source dataset
uspto-grants-2000_08
Patent number
US06107421

Reaction notes

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