N,N,N',N'-Tetramethylethylenediamine → HCID 22609747, compound
Reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1)[CH3:3].CN(CCN(C)C)C.C([Li])CCC.[CH2:25]([Sn:29](Cl)([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH3:28]>CCCCCC>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][N:7]1[C:11]([Sn:29]([CH2:30][CH2:31][CH2:32][CH3:33])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:10][N:9]=[CH:8]1)[CH3:3]Participants
Conditions
- Temperature
- 20 °C
Procedure
1-(N,N-Dimethylaminopropyl)-imidazole (3 g) was added to a mixture of TMEDA (7 ml) and n-butyl lithium (29.4 ml, 1.6 M) in n-hexane (25 ml) at −20° C. under nitrogen. After 30 minutes at −20° C. and 30 minutes at 20° C., the mixture was recooled to −20° C. and tri-n-butylstannyl chloride (13.05 ml) was added dropwise. The mixture was allowed to warm to 20° C. and stirred there for 20 hours. The mixture was partitioned between ethyl acetate and water, the aqueous phase was extracted with ethyl acetate and combined organic extracts were dried and concentrated. Purification by flash chromatography gave the title compound (2.10 g); δH CDCl3 7.70 (1H, s), 7.01 (1H, s), 3.98 (2H, t), 2.20(6H, s), 2.20 (2H, t), 1.90 (2H, m) 1.55 (6H, m), 1.37 (12H, m), 0.92 (9H, m).
Workup
- custom30 minutes
- customat 20° C.
- customwas recooled to −20° C.
- customThe mixture was partitioned between ethyl acetate and water
- extractionthe aqueous phase was extracted with ethyl acetate
- customwere dried
- concentrationconcentrated
- customPurification by flash chromatography
Sources & evidence
- ORD record
- ord-1939b27fe00b4b47947675cb2e171879
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06828320B2
Reaction notes
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