Methyl iodide → 2,2-Dimethyl-4-(4-t-butyldimethylsilyloxybutyl)epsilon-caprolactone

HRID 465565Notes

Reaction equation

HRID 465565 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH3:13][CH:14]1[CH2:21][CH:20]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[CH2:19][CH2:18][O:17][C:15]1=[O:16].CI>O1CCCC1.CCCCCC>[CH3:13][C:14]1([CH3:1])[CH2:21][CH:20]([CH2:22][CH2:23][CH2:24][CH2:25][O:26][Si:27]([C:30]([CH3:32])([CH3:31])[CH3:33])([CH3:29])[CH3:28])[CH2:19][CH2:18][O:17][C:15]1=[O:16]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 100413622-Methyl-4-(4-t-butyldimethylsiloxybutyl)-epsilon-caprolactoneHCID 178418339Butyllithium

Product 1

HCID 99966312,2-Dimethyl-4-(4-t-butyldimethylsilyloxybutyl)epsilon-caprolactone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 10 ml (65 mmol) diisopropylamine in 120 ml dry tetrahydrofuran is added dropwise 26 ml of a 2.5M solution of n-butyllithium in hexane and the mixture is stirred for 15 min. To this solution is added slowly a solution of 10.11 g (32 mmol) of 2-methyl-4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone in 48 ml dry tetrahydrofuran. The mixture is stirred at room temperature for 35 min and 14.0 ml (0.22 mole) of methyl iodide is added rapidly while the flask is cooled in a water bath. After stirring for 3.5 h, the reaction is quenched using saturated ammonium chloride solution and is extracted with ether. The organic phase is washed with water and brine, dried, filtered and concentrated to give an amber oil which is purified by silica gel chromatography using 3:2 hexane/ether to give impure product. Further purification by a second silica gel chromatography using 4:1 hexane/ether as eluent yields 2,2-dimethyl-4-(4-t-butyldimethylsilyloxybutyl)-epsilon-caprolactone; NMR (CDCl3): delta 4.32 (t,2H), 3.6 (t,2H), 1.3 (d,6H), 0.88 (s,9H).

Workup

  1. stirringThe mixture is stirred at room temperature for 35 min
  2. temperatureis cooled in a water bath
  3. stirringAfter stirring for 3.5 h
  4. customthe reaction is quenched
  5. extractionis extracted with ether
  6. washThe organic phase is washed with water and brine
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give an amber oil which
  11. customis purified by silica gel chromatography
  12. customto give impure product
  13. customFurther purification by a second silica gel chromatography

Sources & evidence

ORD record
ord-efb11a01fbf04ad3be9df04eb00f002b
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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