Triethylamine → Diisopropyl-(3-pentynyloxy)silane

HRID 984513Notes

Reaction equation

HRID 984513 reaction equation
[CH2:1]([OH:6])[CH2:2][C:3]#[C:4][CH3:5].C(N(CC)CC)C.Cl[SiH:15]([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:18])[CH3:17]>CN(C)C1C=CN=CC=1.CCCCCC>[CH:16]([SiH:15]([CH:19]([CH3:21])[CH3:20])[O:6][CH2:1][CH2:2][C:3]#[C:4][CH3:5])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 662953-Pentyn-1-olHCID 2758383Chlorodi(isopropyl)silane

Product 1

HCID 59925975Diisopropyl-(3-pentynyloxy)silane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

To a cold (0° C.) solution of 3-pentynol (5.880g, 70.0 mmol, 1.0 equiv), 4-dimethylaminopyridine (DMAP) (840 mg, 7.00 mmol, 0.10 equiv), and triethylamine (TEA) (9.80 ml, 71.0 mmol, 1.01 equiv) in 100 mL of dry hexane was added dropwise chlorodiisopropylsilane (11.0 g, 71.0 mmol, 1.01 equiv) over 20 minutes. The resulting white suspension was allowed to warm to room temperature and was stirred overnight. The reaction mixture was filtered through a short silica pad (10 g) and the solvent was then evaporated in vacuo to give a colorless liquid. Fractional distillation of this liquid afforded 11.2 g (81%) of A-7 as a colorless liquid. An analytical sample (0.48 g) was obtained by redistillation of a 0.50 g sample by Kugelrohr distillation.

Workup

  1. filtrationThe reaction mixture was filtered through a short silica pad (10 g)
  2. customthe solvent was then evaporated in vacuo
  3. customto give a colorless liquid
  4. distillationFractional distillation of this liquid
  5. customafforded 11.2 g (81%) of A-7 as a colorless liquid
  6. customAn analytical sample (0.48 g) was obtained by redistillation of a 0.50 g sample by Kugelrohr distillation

Sources & evidence

ORD record
ord-eba02fa127c64d0dac4a65085aeffd8c
Source dataset
uspto-grants-2005_03
Patent number
US06867323B2

Reaction notes

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