Imidazole → Ethyl 3-((tert-butyldimethylsilyl)oxy)hexanoate

HRID 628930Notes

Reaction equation

HRID 628930 reaction equation
[OH:1][CH:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C.CCOCC>[Si:17]([O:1][CH:2]([CH2:9][CH2:10][CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 61293Ethyl 3-hydroxyhexanoate

Product 1

HCID 14264095Ethyl 3-((tert-butyldimethylsilyl)oxy)hexanoateYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 3-hydroxyhexanoate 1 (2.0 g, 12.5 mmol), imidazole (1.09 g, 18.7 mmol), and tert-butyldimethylsilyl chloride (2.26 g, 15.0 mmol) in DMF (25 mL) was stirred at 23° C. After 16 h the reaction was diluted with Et2O and then washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc) afforded 2.8 g (82%) of silyl ether 2 (see Scheme 1).

Workup

  1. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (silica gel, 100% hex followed by 19:1 hex/EtOAc)

Sources & evidence

ORD record
ord-7f65529dc22c4fb1bd9fece3faf73783
Source dataset
uspto-grants-2016_04
Patent number
US09315486B2

Reaction notes

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