3-Butyn-1-OL → [4-(Triethylsilyl)-3-butyn-1-yloxy]triethylsilane

HRID 1948618Notes

Reaction equation

HRID 1948618 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[Li]CC[CH2:9][CH3:10].[CH2:11]([Si:13]([CH2:17][CH3:18])([CH2:15][CH3:16])Cl)[CH3:12]>C1COCC1>[CH2:11]([Si:13]([CH2:9][CH3:10])([CH2:15][CH3:16])[O:5][CH2:1][CH2:2][C:3]#[C:4][Si:13]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:11][CH3:12])[CH3:12]

Participants

5

Reactant 3

HCID 135663-Butyn-1-OLHCID 13819ChlorotriethylsilaneHCID 178418339Butyllithium

Product 1

HCID 10935420[4-(Triethylsilyl)-3-butyn-1-yloxy]triethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-butin-1-ol (34.99 g, 0.50 mole) was dissolved in THF (1.2 l) under nitrogen and cooled to −30° C. n-BuLi (640 ml, 1.02 mole, 1.6 M solution in n-hexane) was added dropwise to this solution within 15 minutes at such a rate that the temperature did not exceed −20° C. After 1 hour at −20° C. a solution of triethylchlorosilane (171.4 ml, 1.02 mole) in THF (300 ml) was added dropwise within 30 minutes. The cooling bath was removed and the reaction solution was stirred for 15 hours at RT. The reaction mixture was quenched with aqueous Na2CO3 solution (1%) while cooling in an ice bath and was extracted with hexane (2×500 ml). The combined organic phases were washed with saturated NaCl-Solution (300 ml) and dried over MgSO4. After filtering off the drying agent the solvents were removed on a rotary evaporator and the residue was purified by distillation (p=0.05 mbar, head temperature=115°-110° C.), triethyl(4-(triethylsilyl)but-3-inyloxy)silane (88.9 g, 60%) being obtained.

Workup

  1. additionwas added dropwise to this solution within 15 minutes at such a rate that the temperature
  2. customdid not exceed −20° C
  3. customThe cooling bath was removed
  4. customThe reaction mixture was quenched with aqueous Na2CO3 solution (1%)
  5. temperaturewhile cooling in an ice bath
  6. extractionwas extracted with hexane (2×500 ml)
  7. washThe combined organic phases were washed with saturated NaCl-Solution (300 ml)
  8. dry with materialdried over MgSO4
  9. filtrationAfter filtering off the drying agent the solvents
  10. customwere removed on a rotary evaporator
  11. distillationthe residue was purified by distillation (p=0.05 mbar, head temperature=115°-110° C.), triethyl(4-(triethylsilyl)but-3-inyloxy)silane (88.9 g, 60%)
  12. custombeing obtained

Sources & evidence

ORD record
ord-0a48175426074997a96c3eec808ccf0e
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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