Lithium diisopropylamide → HCID 85749769, compound

HRID 277440Notes

Reaction equation

HRID 277440 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. 1H NMR (C6D6): δ 0.9-1.5 (m, Bu), 1.62 (m,—CH2CH2), 3.11 (m, Hγ), 6.26 (dd, J=14.2, 1.5), 6.61 (dd, J=14.2, 4.3); 13C NMR (C6D6): δ 151.0 (Cβ), 126.4 (Cα), 45.1 (Cγ), 33.7 (CH2CH2), 30.0, 27.8, 14.4, 11.4 (Bu); HRMS (El): calculated for C24H41 120Sn2 (M—Bu): 569.1252, found 569.1237.

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-fb9fd1cb27664d2589984d6d37bd607d
Source dataset
uspto-grants-2002_03
Patent number
US06355818B1

Reaction notes

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