Sodium bis(trimethylsilyl)amide → (Z)-3-Ethyl-3-methyl-1-iodo-1-pentene
Reaction equation
[I-].[I:2][CH2:3][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:33]([C:35]([CH3:40])([CH2:38][CH3:39])[CH:36]=O)[CH3:34]>O1CCCC1>[CH2:33]([C:35]([CH3:40])([CH2:38][CH3:39])/[CH:36]=[CH:3]\[I:2])[CH3:34]Participants
5
Conditions
- Temperature
- -78 °C
Procedure
A suspension of (iodomethyl)triphenylphosphonium iodide (0.530 g, 1 mmol) in tetrahydrofuran (3 mL) was treated dropwise at room temperature with sodium bis(trimethylsilyl)amide (1 mL, 1M solution in THF, 1 mmol) for 2-3 minutes. The solution was then cooled to −78° C. and a solution of 2-ethyl-2-methyl-butanal (0.100 g, 0.88 mmol) in tetrahydrofuran was added dropwise. The cooling bath was removed and stirring continued at room temperature for 1 hour. The reaction mixture was diluted with hexane, filtered and evaporated. The crude compound was purified by silica gel chromatography (hexane) and afforded the title compound (0.130 g, 62%).
Workup
- customThe cooling bath was removed
- additionThe reaction mixture was diluted with hexane
- filtrationfiltered
- customevaporated
- customThe crude compound was purified by silica gel chromatography (hexane)
Sources & evidence
- ORD record
- ord-d1d9e937a7434cb29c82c54ec7cda618
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06194601B1
Reaction notes
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