Chlorodimethylaluminum → (R)-1-Chloro-6-trimethylsilanyl-hex-4-yn-2-ol
Reaction equation
[CH2:1]([Si:4]([CH3:7])([CH3:6])[CH3:5])[C:2]#[CH:3].[Li]CCCC.[Al](Cl)(C)C.[CH2:17]([C@@H:19]1[O:21][CH2:20]1)[Cl:18]>C1(C)C=CC=CC=1>[Cl:18][CH2:17][C@H:19]([OH:21])[CH2:20][C:3]#[C:2][CH2:1][Si:4]([CH3:7])([CH3:6])[CH3:5]Participants
Procedure
14.11 g (126 mmol) of propargyltrimethylsilane was dissolved in 125 ml of abs. toluene and cooled to -17°. 81.1 ml of nBuLi (1.55 M, hexane) was slowly added while keeping the temperature below -5°. 5 Minutes later, 126 ml of Me2AlCl (1 M, hexane) was added to this solution of the Li-acetylide. The temperature was then lowered to -45° and 6.90 ml of (R)-epichlorohydrine (88 mmol), dissolved in 50 ml of toluene, was added. The cooling bath was then removed and the reaction mixture allowed to reach ambient temperature during 24h. After careful quenching with icecold water and filtration, the product was extracted with ether, washed with NH4Cl, dried over sodium sulfate and the solvents removed i. V. Flash chromatography (SiO2, hexane/AcOEt=86/14) yielded 12.01 g of (R)-1-chloro-6-trimethylsilanyl-hex-4-yn-2-ol as colorless oil, 97% pure according to GC.
Workup
- customthe temperature below -5°
- customwas then lowered to -45°
- additionwas added
- customThe cooling bath was then removed
- customAfter careful quenching with icecold water and filtration
- extractionthe product was extracted with ether
- washwashed with NH4Cl
- dry with materialdried over sodium sulfate
- customthe solvents removed i
Sources & evidence
- ORD record
- ord-b676aca0d32548d08e433deab0417857
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05994569
Reaction notes
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