Imidazole → HCID 10925936, compound

HRID 2275437Notes

Reaction equation

HRID 2275437 reaction equation
N1C=CN=C1.[CH2:6]([OH:12])[CH2:7][CH2:8][CH2:9][CH2:10][OH:11].[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14]>ClCCl>[Si:17]([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][OH:12])([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 81051,5-PentanediolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 10925936HCID 10925936, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Imidazole (0.65 g, 9.60 mmol) was added to a stirring solution of pentan-1,5-diol (1.00 g, 9.60 mmol) in dry dichloromethane (10 mL) at 0° C. under an argon atmosphere followed by the dropwise addition of tert-butylchlorodiphenylsilane (3.85 mL, 9.60 mmol) in CH2Cl2 (2 mL). The reaction was allowed to slowly reach room temperature. After 12 hours, the reaction mixture was washed with water (2×30 mL), brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue which was purified by SiO2 flash chromatography using 30% ethyl acetate/hexane as eluent to furnish 2 (1.35 g, 46%), recovered SM and di-protected compound. TLC: 30% EtOAc/hexanes, Rf˜0.38; 1H NMR (CDCl3, 400 MHz) δ 7.67-7.62 (m, 4H), 7.45-7.35 (m, 6H), 3.67 (t, 2H, J=6.0 Hz), 3.52 (t, 2H, J=6.7 Hz), 2.03-1.93 (m, 2H), 1.72-1.64 (m, 4H), 1.04 (s, 9H).

Workup

  1. customwas allowed to slowly reach room temperature
  2. washthe reaction mixture was washed with water (2×30 mL), brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue which was purified by SiO2 flash chromatography

Sources & evidence

ORD record
ord-7a2f3eedf70e4ff090de0f3871a99410
Source dataset
uspto-grants-2015_09
Patent number
US09127027B2

Reaction notes

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