Triethylamine → tert-Butyldimethyl-[1-(1-propylcyclobutyl)but-3-ynyloxy]silane

HRID 2249571Notes

Reaction equation

HRID 2249571 reaction equation
[Si:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:23]([C:26]1([CH:30](O)[CH2:31][C:32]#[CH:33])[CH2:29][CH2:28][CH2:27]1)[CH2:24][CH3:25].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:4]([Si:1]([CH3:3])([CH3:2])[O:8][CH:30]([C:26]1([CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28][CH2:29]1)[CH2:31][C:32]#[CH:33])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 516892Sodium BicarbonateHCID 142547761-(1-Propylcyclobutyl)but-3-yn-1-ol

Product 1

HCID 15475299tert-Butyldimethyl-[1-(1-propylcyclobutyl)but-3-ynyloxy]silaneYield 153.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyldimethylsilyltrifluoromethanesulfonate (1.8 mL, 7.88 mmol) was added to a solution of triethylamine (2.2 mL, 15.8 mmol) and alcohol 4 (650 mg, 3.94 mmol) in CH2Cl2 (5.0 mL) at 0° C. The reaction was stirred for 1 h and then saturated aqueous NaHCO3 was added. The mixture was extracted with CH2Cl2. The organic portion was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. FCC (silica gel, 100% hexane) gave 1.7 g (100%) of the silyl ether 5 as a clear, colorless oil.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washThe organic portion was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0331834af2524f36beffdf98d9322b2e
Source dataset
uspto-grants-2008_01
Patent number
US07314890B2

Reaction notes

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