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

HRID 465563Notes

Reaction equation

HRID 465563 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>[Si:19]([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)([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 h. 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-butyldimethylsilyloxybutyl)-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-aa6087f6a63749b68e65c1004410cb7f
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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