Dimethylformamide → HCID 178482623, compound

HRID 1014754Notes

Reaction equation

HRID 1014754 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.C[CH2:20][O:21]CC.[Li]CCCC.CN(C=O)C>C1COCC1>[CH:20]([C:5]1[C-:4]([N:2]([CH3:3])[CH3:1])[CH:8]=[CH:7][CH:6]=1)=[O:21].[CH-:9]1[CH:13]=[CH:12][CH:11]=[CH:10]1.[Fe+2:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8000Boron trifluoride etherateHCID 129678476cyclopenta-1,3-diene;N,N-dimethylcyclopenta-2,4-dien-1-amine;iron(2+)HCID 178418339Butyllithium

Product 1

HCID 178482623HCID 178482623, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 (100 mg, 0.44 mmol) in THF (5 mL) was sequentially treated with BF3.OEt2 (58 μL, 0.46 mmol), n-BuLi (0.51 mL, 1.70 M, 0.87 mmol) and DMF (0.17 mL, 2.18 mmol). Standard workup followed by gradient column chromatography (silica gel, 94:5:1 hexanes/Et2O/Et3N, then 84:15:1 hexanes/Et2O/Et3N) gave 12d (85 mg, 76%) as a red-orange oil; IR (KBr, neat) vmax 3097, 2943, 2851, 2826, 2785, 1667 cm−1, 1H NMR (300 MHz, CDCl3) 10.13 (s, 1H), 4.61 (m, 1H), 4.40 (t, 1H, J=2.7 Hz), 4.29 (m, 1H), 4.27 (s, 5H), 2.70 (s, 6H) ppm; 13C NMR (75.5 MHz, CDCl3) 192.8, 117.5, 71.8, 69.5, 67.7, 66.2, 60.2, 45.6 ppm; EIMS [m/z (%)] 257 (M+, 100), 229 (13), 119 (54), 44 (66); HRMS (EI) calcd for C13H15NO56Fe: 257.0503. Found 257.0504.

Sources & evidence

ORD record
ord-aaba26ea110e4d1abc96ebbf57443f6d
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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