Boron trifluoride etherate → HCID 178482628, compound

HRID 1014757Notes

Reaction equation

HRID 1014757 reaction equation
[CH3:1][N:2]([C-:4]1[CH:8]=[CH:7][CH:6]=[CH:5]1)[CH3:3].[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14].B(F)(F)F.CCOCC.[Li]CCCC.[Sn:29](Cl)([CH3:32])([CH3:31])[CH3:30]>C1COCC1>[CH3:30][Sn:29]([CH3:32])([CH3:31])[C:5]1[C-:4]([N:2]([CH3:3])[CH3:1])[CH:8]=[CH:7][CH:6]=1.[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 14016Trimethyltin chlorideHCID 129678476cyclopenta-1,3-diene;N,N-dimethylcyclopenta-2,4-dien-1-amine;iron(2+)HCID 178418339Butyllithium

Product 1

HCID 178482628HCID 178482628, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 (300 mg, 1.31 mmol) in THF (13 mL) was sequentially treated with BF3.OEt2 (0.17 mL, 1.37 mmol), n-BuLi (0.59 mL, 2.45 M, 1.44 mmol) and Me3SnCl (1.57 mL, 1.57 mmol). Standard workup followed by column chromatography (basic alumina, hexanes) gave 12h (466 mg, 91%) as an orange oil; IR (KBr, neat) vmax 3093, 2980, 2940, 2910, 2825, 2775 cm−1; 1H NMR (300 MHz, CDCl3) 4.16 (s, 6H), 4.06 (m, 1H), 3.81 (m, 1H), 2.59 (s, 6H), 0.32 (s, 9H) ppm; 13C NMR (75.5 MHz, CDCl3) 120.2, 70.9, 67.8, 66.4, 60.4, 58.0, 45.1, −7.6 ppm; EIMS [m/z (%)] 393 (M+, 100), 348 (88); HRMS (EI) calcd for C15H23N118Sn56Fe: 391.0198. Found 391.0194.

Sources & evidence

ORD record
ord-a410d01936054ac0acb0b20357901f5c
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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