Imidazole → Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane

HRID 2203662Notes

Reaction equation

HRID 2203662 reaction equation
[OH:1][CH:2]1[CH2:6][CH:5]=[CH:4][CH2:3]1.N1C=CN=C1.[Si:12](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C=O.O.C(OCC)(=O)C>[C:25]([Si:12]([O:1][CH:2]1[CH2:6][CH:5]=[CH:4][CH2:3]1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 2814783-Cyclopenten-1-ol

Product 1

HCID 11347853Tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilaneYield 89,679.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice-cooled solution of 4-hydroxycyclopentene (50.0 g, 0.594 mol) and imidazole (80.9 g, 1.19 mol) in N,N-dimethylformamide (300 mL) was slowly added tert-butyldiphenylsilyl chloride (180 g, 0.65 mmol). The reaction mixture was warmed to room temperature. After 16 h, the reaction mixture was diluted with water (1 L) and ethyl acetate (500 mL). The aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organics were washed sequentially with water (3×300 mL) and saturated aqueous sodium chloride solution (2×200 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (15:1 petroleum ether/ethyl acetate) provided tert-butyl(cyclopent-3-en-1-yloxy)diphenylsilane (188 g, 98%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.69-7.66 (m, 4H), 7.43-7.38 (m, 6H), 5.63-5.60 (m, 2H), 4.58-4.53 (m, 1H), 2.46-2.38 (m, 4H), 1.61 (s, 9H).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×200 mL)
  2. washThe combined organics were washed sequentially with water (3×300 mL) and saturated aqueous sodium chloride solution (2×200 mL)
  3. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography (15:1 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-cfc09d13171349a0856841c1715826ea
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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