Imidazole → Methyl 5-(tert-butyl-dimethylsilyl)oxypentanoate

HRID 1098136

Reaction equation

HRID 1098136 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].N1C=CN=C1>C(Cl)Cl>[Si:5]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 3014818Pentanoic acid, 5-hydroxy-, methyl ester

Product 1

HCID 11139432Methyl 5-(tert-butyl-dimethylsilyl)oxypentanoateYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of tert-butylchlorodimethylsilane (27.1 g, 179.79 mmol) in DCM (50 mL) was added dropwise to a stirred solution of methyl 5-hydroxypentanoate (CAS no. 14273-92-8, Huckstep, M.; Taylor, R. J. K.; Caton, M. P. L. Synthesis 1982, 10, 881) (19.8 g, 149.82 mmol) and 1H-imidazole (15.30 g, 224.73 mmol) in DCM (200 mL) at 5° C., over a period of 10 minutes under nitrogen. The resulting suspension was stirred at ambient temperature for 6 hours. The reaction mixture was diluted with DCM (250 mL), and washed sequentially with water (2×200 mL) and saturated brine (200 mL). The organic layer was dried (MgSO4) and evaporated. The residue was purified by flash silica chromatography, eluting with 10 to 50% ethyl acetate in isohexane to afford the product (19.3 g, 52%).

Workup

  1. washwashed sequentially with water (2×200 mL) and saturated brine (200 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by flash silica chromatography
  5. washeluting with 10 to 50% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-c3e8a6411ea7432b85eed9fffce967b1
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Linked notes

Loading…