Triethylamine → (But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

HRID 515058Notes

Reaction equation

HRID 515058 reaction equation
[CH:1]#[C:2][CH2:3][CH2:4][OH:5].[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:9]([Si:6]([O:5][CH2:4][CH2:3][C:2]#[CH:1])([CH3:8])[CH3:7])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, 0° C. solution of homopropargyl alcohol (10 g, 0.14 mol) and tert-butyldimethylsilyl chloride (21.5 g, 0.14 mol) in dichloromethane (50 mL) was treated with triethylamine (22.8 mL, 0.168 mol). The mixture was then stirred overnight at room temperature. The mixture was washed with water and the organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography (95:5 hexane/ethyl acetate) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 0.08 (s, 6H), 0.90 (s, 9H), 1.96 (t, J=3 Hz, 1H), 2.41 (dt, J=6 Hz, J=3 Hz, 2H), 3.75 (d, J=6 Hz, 2H).

Workup

  1. washThe mixture was washed with water
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by chromatography (95:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5b89ff268b8b481c8951044517b33448
Source dataset
uspto-grants-2015_08
Patent number
US09108948B2

Reaction notes

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