Imidazole → (R)-Methyl 6-((tert-butyldimethylsilyl)oxy)heptanoate

HRID 628942Notes

Reaction equation

HRID 628942 reaction equation
[OH:1][C@H:2]([CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].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][C@H:2]([CH3:11])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 118036747(R)-methyl 6-hydroxyheptanoate

Product 1

HCID 125473334(R)-Methyl 6-((tert-butyldimethylsilyl)oxy)heptanoateYield 71.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of alcohol 25 (2.53 g, 15.89 mmol), imidazole (1.9 g, 27.9 mmol), and tert-butyldimethylsilyl chloride (2.4 g, 15.89 mmol) in DMF (32 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, 9:1 hex/EtOAc) afforded 3.11 g (71%) of silyl ether 26 (see scheme 4).

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, 9:1 hex/EtOAc)

Sources & evidence

ORD record
ord-5f7e20249d7449d1adb170a2485467a7
Source dataset
uspto-grants-2016_04
Patent number
US09315486B2

Reaction notes

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