Chlorotrimethylsilane → HCID 178482627, compound

HRID 1014753Notes

Reaction equation

HRID 1014753 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.[CH3:29][Si:30](Cl)([CH3:32])[CH3:31]>C1COCC1>[CH3:29][Si:30]([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 6397ChlorotrimethylsilaneHCID 8000Boron trifluoride etherateHCID 129678476cyclopenta-1,3-diene;N,N-dimethylcyclopenta-2,4-dien-1-amine;iron(2+)HCID 178418339Butyllithium

Product 1

HCID 178482627HCID 178482627, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11 (229 mg, 1.0 mmol) in THF (10 mL) was sequentially treated with BF3.OEt2 (0.13 mL, 1.05 mmol), n-BuLi (0.48 mL, 2.30 M, 1.10 mmol) and TMSCl (0.15 mL, 1.20 mmol). Standard workup followed by column chromatography (silica gel, 7:3 hexanes/Et2O, Rf=0.68) gave 12a (279 mg, 93%) as an orange oil; IR (KBr, neat) max 3096, 2952, 2818, 2774, 1247 cm−1; 1H NMR (300 MHz, CDCl3) 4.16 (s, 5H), 4.13 (t, 1H, J=2.7 Hz), 4.10 (m, 1H), 3.86 (m, 1H), 2.57 (s, 6H), 0.33 (s, 9H) ppm; 13C NMR (75.5 MHz, CDCl3) 120.1, 70.6, 68.5, 66.2, 65.9, 58.0, 46.1, 0.5 ppm; EIMS [m/z(%)] 301 (M+, 100); HRMS (EI) calcd for C15H23N28Si56Fe: 301.0949. Found 301.0945.

Sources & evidence

ORD record
ord-7a8a18d48dd047d6bf3d465d00626df9
Source dataset
uspto-grants-2011_07
Patent number
US07982064B2

Reaction notes

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