Imidazole → Silane, (1,1-dimethylethyl)(5-hexynyloxy)diphenyl-

HRID 2275436Notes

Reaction equation

HRID 2275436 reaction equation
[C:1]([Si:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([OH:25])[CH2:20][CH2:21][CH2:22][C:23]#[CH:24].N1C=CN=C1>C(Cl)Cl>[Si:5]([O:25][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[CH:24])([C:1]([CH3:4])([CH3:3])[CH3:2])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 702345-Hexyn-1-olHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 11823921Silane, (1,1-dimethylethyl)(5-hexynyloxy)diphenyl-Yield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyldiphenylchlorosilane (3.2 mL, 12.4 mmol) was added dropwise to a stirring, 0° C. solution of 5-hexyn-1-ol (4, 1.07 g, 10.9 mmol) and anhydrous imidazole (1.84 g, 27.1 mmol) in anhydrous CH2Cl2 (20 mL) under an argon atmosphere. After complete addition, the reaction mixture was stirred at room temperature for 12 hours, then quenched with saturated aq. NH4Cl solution (50 mL) and extracted with Et2O (3×50 mL). The combined ethereal extracts were washed with saturated aq. NaCl solution (25 mL), dried over NaSO4, and the solvent was removed in vacuo. The residue was purified by flash chromatography (5% ethyl acetate/hexane) to yield 1-tert-butyldiphenylsilyloxy-hex-5-yne (5) (3.54 g, 10.5 mmol, 96%) as a colorless oil. TLC: 5% EtOAc/hexanes, Rf≈0.65; 1H NMR (400 MHz, CDCl3) δ 7.77-7.65 (m, 4H), 7.40-7.30 (m, 6H), 3.70 (t, 2H, J=5.6 Hz), 2.40-2.25 (m, 2H), 2.05 (t, 1H, J=2.8 Hz), 1.90-1.70 (m, 4H), 1.18 (s, 9H).

Workup

  1. additionAfter complete addition
  2. customquenched with saturated aq. NH4Cl solution (50 mL)
  3. extractionextracted with Et2O (3×50 mL)
  4. washThe combined ethereal extracts were washed with saturated aq. NaCl solution (25 mL)
  5. dry with materialdried over NaSO4
  6. customthe solvent was removed in vacuo
  7. customThe residue was purified by flash chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1e9b3b033a65464b8490540ee4b3515c
Source dataset
uspto-grants-2015_09
Patent number
US09127027B2

Reaction notes

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