Imidazole → 4-(4-t-Butyldimethylsiloxybutyl)-epsilon-caprolactone

HRID 1494108Notes

Reaction equation

HRID 1494108 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:13][CH2:12][O:11][C:9](=[O:10])[CH2:8][CH2:7]1.N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>CN(C)C=O>[O:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[CH2:13][CH2:12][O:11][C:9](=[O:10])[CH2:8][CH2:7]1)[Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 103300695-(4-Hydroxybutyl)oxepan-2-one

Product 1

HCID 99720434-(4-t-Butyldimethylsiloxybutyl)-epsilon-caprolactone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8.77 g (47 mmol) of 4-(4-hydroxybutyl)-epsilon-caprolactone (Example 28) in 52 mL dry dimethylformamide is added 6.16 g (90 mmol) of imidazole followed by 11.1 g (71 mmol) of t-butyldimethylsilyl chloride (97% pure) and then the mixture is stirred for 16 hours. The reaction mixture is poured into water and extracted twice with ether. The combined organic extracts are washed twice with water, brine, dried, filtered and concentrated to give an oil which is purified by flash chromatography using 3:2 hexane/ether to yield 4-(4-t-butyldimethylsiloxybutyl)-epsilon-caprolactone as an oil; NMR (CDCl3): delta 4-4.3 (m,2H), 3.6 (t,2H), 0.88 (s,9H).

Workup

  1. extractionextracted twice with ether
  2. washThe combined organic extracts are washed twice with water, brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil which
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-ba1137480e1841ee9ce9dcfd29780c89
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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