Water → HCID 57386253, compound

HRID 2406856Notes

Reaction equation

HRID 2406856 reaction equation
[CH2:1]=[CH:2][C@@H:3]([OH:8])[CH2:4][CH2:5][C:6]#[CH:7].C(N(CC)CC)C.O([Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])S(C(F)(F)F)(=O)=O.O>C(Cl)Cl>[C:27]([Si:24]([CH3:26])([CH3:25])[O:8][C@H:3]([CH:2]=[CH2:1])[CH2:4][CH2:5][C:6]#[CH:7])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 57385997HCID 57385997, compound

Product 1

HCID 57386253HCID 57386253, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The crude (S)-hept-1-en-6-yne-3-ol (3a) was dissolved in DCM and cooled to 0° C. Triethylamin (1.55 mL, 1.132 g, 11.182 mmol) and tert-Butyldimethylsilyl triflate (2.15 mL, 2.475 g, 9.362 mmol) were added and the solution was stirred for 1 hour at 0° C. before it was warmed to room temperature. After stirring for another hour water was added and the solution was extracted with DCM (3×). The combined organic phases were washed with brine, dried (Na2SO4) and concentrated in vacuo. Chromatography (pentane/ether 200/1) furnished 489 mg of compound (4a) as clear colourless oil with 58% yield.

Workup

  1. temperaturewas warmed to room temperature
  2. additionwas added
  3. extractionthe solution was extracted with DCM (3×)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-682d24df88e547c6965dbd916b5a7bb9
Source dataset
uspto-grants-2014_08
Patent number
US08809395B2

Reaction notes

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