1,1,3,3-Tetramethyldisilazane, 97% → HCID 66722559, compound

HRID 1640054Notes

Reaction equation

HRID 1640054 reaction equation
[CH3:1][C:2](=[CH2:7])[C:3]#[C:4][CH2:5][OH:6].[CH3:8][SiH:9]([CH3:14])N[SiH](C)C.CC([O-])(C)C.[K+]>>[CH3:8][Si:9]1([CH3:14])[C:3]([C:2]([CH3:1])=[CH2:7])=[CH:4][CH2:5][O:6]1

Participants

4

Reactant 3

HCID 851961,1,3,3-Tetramethyldisilazane, 97%HCID 108878354-methyl-4-penten-2-yn-1-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 66722559HCID 66722559, compoundYield 115.7%

Procedure

Using 4-methylpent-4-en-2-yn-1-ol (1.792 g, 18.64 mmol), 1,1,3,3-tetramethyldisilazane (1.504 g, 11.28 mmol) and KOtBu (0.217 g, 1.934 mmol) according to the above general procedure resulted a clear brown colored crude reaction mixture which upon purification by column chromatography yielded 10a as a clear colorless oil (2.014 g, 13.05 mmol, 70.0%): Rf 0.68 (pentane/Et2O, 3:1); 1H NMR (500 MHz, CDCl3) δ 6.60 (as, 1H, H-4), 4.99 (s, 1H, H-8′), 4.82 (s, 1H, H-8″), 4.66 (s, 2H, H-5), 1.93 (s, 3H, H-9), 0.33 (as, 6H, H-6); 13C NMR (300 MHz, CDCl3) δ 142.2 (C-3), 141.3 (C-7), 141.2 (C-4), 115.7 (C-8), 71.9 (C-5), 20.4 (C-9), 0.45 (C-6); HRMS calcd for C8H14OSi (M+) 154.0814. found 154.0813.

Workup

  1. customresulted a clear brown colored crude
  2. customreaction mixture which
  3. customupon purification by column chromatography

Sources & evidence

ORD record
ord-ade58405c48e4809aa594753637b490e
Source dataset
uspto-grants-2012_02
Patent number
US08110695B2

Reaction notes

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