Imidazole → Ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}hexanoate

HRID 1098072Notes

Reaction equation

HRID 1098072 reaction equation
N1C=CN=C1.[CH3:6][C:7]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH2:14]([O:16][C:17](=[O:24])[CH:18]([OH:23])[CH2:19][CH2:20][CH2:21][CH3:22])[CH3:15].O>CN(C=O)C.C(OCC)C>[Si:10]([O:23][CH:18]([CH2:19][CH2:20][CH2:21][CH3:22])[C:17]([O:16][CH2:14][CH3:15])=[O:24])([C:7]([CH3:9])([CH3:8])[CH3:6])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 103589Hexanoic acid, 2-hydroxy-, ethyl ester

Product 1

HCID 57438620Ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}hexanoateYield 96.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Imidazole (4.10 g, 60.22 mmol) and TBDMSCl (3.60 g, 23.89 mmol) was added to a stirred solution of 2-hydroxy-hexanoic acid ethyl ester (3.20 g, 19.97 mmol) in DMF (25 mL). The reaction mixture was kept at ambient temperature for 18 hrs. Water and diethyl ether were added and the two phases were separated. The aqueous phase was extracted with diethyl ether. The organic extracts were combined and washed sequentially with 0.5 M HCl and water, dried over MgSO4 and concentrated in vacuo to give the title product (5.30 g), 1H NMR (300 MHz, CDCl3) δ 4.18 (m, 3H), 1.69 (m, 2H), 1.35 (m, 4H), 1.28 (t, 3H), 0.91 (m, 12H), 0.07 (d, 6H).

Workup

  1. customthe two phases were separated
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. washwashed sequentially with 0.5 M HCl and water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2ac5d7dbb0bb42be8466d81fe25e496e
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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