Boron trifluoride → (S)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol

HRID 335631

Reaction equation

HRID 335631 reaction equation
C([Li])(C)(C)C.[Si:6]([C:10]#[CH:11])([CH3:9])([CH3:8])[CH3:7].[C:12]([Si:16]([CH3:23])([CH3:22])[O:17][CH2:18][C@@H:19]1[CH2:21][O:20]1)([CH3:15])([CH3:14])[CH3:13].B(F)(F)F>C1COCC1>[Si:16]([O:17][CH2:18][C@@H:19]([OH:20])[CH2:21][C:11]#[C:10][Si:6]([CH3:9])([CH3:8])[CH3:7])([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 66111TrimethylsilylacetyleneHCID 10954307(S)-Glycidoxy-t-butyldimethylsilaneHCID 178418306HCID 178418306, compound

Product 1

HCID 86667886(S)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

tert-Butyl lithium (2 eq) is added to a solution of TMS-acetylene (2 eq) in THF at −78° C. and the reaction mixture stirred for an additional 30 min. (S)-tert-butyldimethyl(oxiran-2-ylmethoxy)silane (1 eq) and BF3.EtO2 (2 eq) are added and stirred at −78° C. for 4.5 hours. The reaction is quenched by addition of aqueous ammonium chloride solution and extracted with ethyl acetate (3×). The combined organic layers are washed with brine, dried (MgSO4) and concentrated under reduced pressure to afford (S)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol.

Workup

  1. additionEtO2 (2 eq) are added
  2. customThe reaction is quenched by addition of aqueous ammonium chloride solution
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c650cd2575384df8b1b59e540ce46b40
Source dataset
uspto-grants-2014_11
Patent number
US08884058B2

Linked notes

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