Imidazole → Butyl 2-(tert-butyldimethylsilyloxy)acetate

HRID 324272

Reaction equation

HRID 324272 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH2:2][OH:3].N1C=CN=C1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16]>CCOCC.CCCCCC>[C:15]([Si:19]([CH3:22])([CH3:21])[O:3][CH2:2][C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 81882Butyl Glycolate

Product 1

HCID 14079954Butyl 2-(tert-butyldimethylsilyloxy)acetate

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

n-Butyl glycolate (231 g; 1.75 mol) and imidazole (345.1 g; 5.07 mol) were combined at 0° C. The suspension obtained was treated portionwise with t-butyldimethylchlorosilane (303 g; 2.01 mol) over 1.5 hours. After 20 hours at room temperature the reaction mixture was diluted with ether/n-hexane 1:1 (1 l) and suction filtered. The crystals were rinsed thoroughly with ether/n-hexane 1:1 (200 ml). The filtrate was washed in succession with water (2×700 ml) and saturated aqueous sodium chloride solution (500 ml), dried over magnesium sulphate and concentrated. The oil obtained was distilled over a Vigreux column (7.5 cm). Yield: 405 g (94%) as a colorless oil (b.p. 78° C./0.98 mm Hg).

Workup

  1. customwere combined at 0° C
  2. customThe suspension obtained
  3. filtrationfiltered
  4. washThe crystals were rinsed thoroughly with ether/n-hexane 1:1 (200 ml)
  5. washThe filtrate was washed in succession with water (2×700 ml) and saturated aqueous sodium chloride solution (500 ml)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated
  8. customThe oil obtained
  9. distillationwas distilled over a Vigreux column (7.5 cm)

Sources & evidence

ORD record
ord-a836643b65db45459e454d5770294002
Source dataset
uspto-grants-2001_04
Patent number
US06218379B1

Linked notes

Loading…