Tetrahydrofuran → 8-(t-Butyldimethylsilyloxy)-1-octyne

HRID 1792347Notes

Reaction equation

HRID 1792347 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].O1CC[CH2:18][CH2:17]1>CS(C)=O>[Si:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:17]#[CH:18])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilane

Product 1

HCID 104217908-(t-Butyldimethylsilyloxy)-1-octyneYield 73.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
4 °C

Procedure

6-Bromo-1-(t-butyldimethylsilyloxy)hexane (20 g, 110.42 mmol) was dissolved in dry dimethyl sulfoxide (500 ml) and tetrahydrofuran (50 ml) and cooled to 0° C. under argon atmosphere, to which was added lithium acetylide ethylene diamine complex (28.0 g, 304.74 mmol) and the resulting solution was stirred for 1 day at 4° C. After the reaction was completed, the mixture was poured in ice-water and extracted with ethyl ether. The organic solvent was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. This crude product was purified by column chromatography on silica gel, eluting with ethyl acetate:n-hexane=1:40. After removal of the solvent, 18 g of the title compound was obtained as colorless oil. (yield: 73.8%)

Workup

  1. additionwas added lithium acetylide ethylene diamine complex (28.0 g, 304.74 mmol)
  2. extractionextracted with ethyl ether
  3. dry with materialThe organic solvent was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThis crude product was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-e7eed1790609489187af49b9eb17f211
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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