Hydrochloric Acid → 4-(Triethylsilyl)-3-butyn-1-ol

HRID 1948619Notes

Reaction equation

HRID 1948619 reaction equation
C([Si](CC)(CC)[O:4][CH2:5][CH2:6][C:7]#[C:8][Si:9]([CH2:14][CH3:15])([CH2:12][CH3:13])[CH2:10][CH3:11])C.Cl.CCCCCC.O>CO>[CH2:14]([Si:9]([CH2:10][CH3:11])([CH2:12][CH3:13])[C:8]#[C:7][CH2:6][CH2:5][OH:4])[CH3:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8058HexaneHCID 10935420[4-(Triethylsilyl)-3-butyn-1-yloxy]triethylsilane

Product 1

HCID 27606944-(Triethylsilyl)-3-butyn-1-olYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethyl(4-(triethylsilyl)but-3-inyloxy)silane (32.99 g, 110.66 mmole) was dissolved in MeOH (336 ml), 2N HCl (62 ml) was added, and the mixture was stirred for 4 hours at RT. Hexane (250 ml) and H2O (200 ml) were then added to the solution and the aqueous phase was extracted with hexane (3×100 ml). The combined organic phases were washed with H2O (100 ml) and then with saturated NaCl-Solution (50 ml) and dried over MgSO4. After filtering off the drying agent the solvents were removed on a rotary evaporator. Column chromatography of the residue (hexane/ether=4:1, then ether) yielded 4-(triethylsilyl)but-3-in-1-ol (19.6 g, 96%) as a colourless oil.

Workup

  1. extractionthe aqueous phase was extracted with hexane (3×100 ml)
  2. washThe combined organic phases were washed with H2O (100 ml)
  3. dry with materialwith saturated NaCl-Solution (50 ml) and dried over MgSO4
  4. filtrationAfter filtering off the drying agent the solvents
  5. customwere removed on a rotary evaporator

Sources & evidence

ORD record
ord-5556131f643c484d839d5fa79dc7d92b
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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