Dimethylformamide → tert-Butyl-dimethyl-(1-methyl-1-propyl-prop-2-ynyloxy)-silane

HRID 250535Notes

Reaction equation

HRID 250535 reaction equation
[CH3:1][C:2]([OH:8])([CH2:5][CH2:6][CH3:7])[C:3]#[CH:4].CN(C=O)C.CCN(CC)CC.FC(F)(F)S(O[Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])(=O)=O>CCOC(C)=O>[C:30]([Si:27]([CH3:29])([CH3:28])[O:8][C:2]([CH3:1])([CH2:5][CH2:6][CH3:7])[C:3]#[CH:4])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 203473-Methyl-1-hexyn-3-olHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Product 1

HCID 85825722tert-Butyl-dimethyl-(1-methyl-1-propyl-prop-2-ynyloxy)-silaneYield 100.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An oven dried flask was charged with 3-methyl-hex-1-yn-3-ol (1.02 g, 0.009 mol) and dry DMF (9.0 mL). To this solution, cooled in an ice bath, was added Et3N (4.6 mL, 0.033 mol) followed by dropwise addition of tert-butyldimethylsilyl trifluoromethanesulfonate (2.9 g, 0.016 mol) under nitrogen atmosphere. The resulting mixture was stirred at RT for 18 h and then diluted with EtOAc (50 mL). The organic layer was washed with a saturated solution of NH4Cl (30 mL), water (4×20 mL), brine (40 mL), dried over sodium sulfate, and evaporated to afford the desired compound (2.05 g, 99.6%), as a yellow oil, used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.152 (s, 3H), 0.156 (s, 3H), 0.85-0.84 (m, 9H), 0.91 (t, J=6.69 Hz, 3H), 1.41 (s, 3H), 1.61-1.44 (m, 4H), 3.37 (s, 1H).

Workup

  1. customAn oven dried flask
  2. temperatureTo this solution, cooled in an ice bath
  3. washThe organic layer was washed with a saturated solution of NH4Cl (30 mL), water (4×20 mL), brine (40 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-75a138471c02492b9239f938afb4b92a
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

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