Imidazole → HCID 90353205, compound

HRID 628819Notes

Reaction equation

HRID 628819 reaction equation
[OH:1][C@H:2]([CH2:8][C:9](=[O:11])[CH3:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C>[O:1]([C@H:2]([CH2:8][C:9](=[O:11])[CH3:10])[CH2:3][C:4]([O:6][CH3:7])=[O:5])[Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11019155HCID 11019155, compound

Product 1

HCID 90353205HCID 90353205, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl(3R)-3-hydroxy-5-oxohexanoate (6) (10 g, 0.062 mol) was dissolved in dry DMF (110 mL) and the solution was cooled down to 0° C. Imidazole (8.5 g, 0.124 mol) and tert-butyldimethylsilyl chloride (11.3 g, 0.0744 mol) were added. The reaction mixture was stirred at 25° C. for 12 h and then quenched with a 10% NaHCO3 solution. After the extraction with toluene (3×150 mL), the collected organic phase was dried under vacuum and the resulted oil was purified via by fractional distillation. Methyl(3R)-3-(tert-butyldimethylsiloxy)-5-oxohexanoate was obtained as a yellow oil the compound of formula (II-R, PG=TDBMS, Z=OMe)(11.3 g; molar yield 66%).

Workup

  1. customquenched with a 10% NaHCO3 solution
  2. extractionAfter the extraction with toluene (3×150 mL)
  3. customthe collected organic phase was dried under vacuum
  4. distillationthe resulted oil was purified via by fractional distillation

Sources & evidence

ORD record
ord-c06e6657bb1e4de790a062b3b1ead2e5
Source dataset
uspto-grants-2016_04
Patent number
US09315470B2

Reaction notes

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