Imidazole → HCID 53653299, compound

HRID 733335Notes

Reaction equation

HRID 733335 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:9]([O:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])=[CH:19][C:18]=1[OH:33])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CN=C1.O>ClCCl>[Si:1]([O:33][C:18]1[CH:19]=[C:20]([CH:31]=[CH:32][C:17]=1[O:16][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 54394841HCID 54394841, compound

Product 1

HCID 53653299HCID 53653299, compoundYield 108.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyldimethylsilyl chloride (579 mg, 3.84 mmol) in dichloromethane (10 cm3) was added to a stirred solution of benzyl 4-benzyloxy-3-hydroxy-benzoate (642.3 mg, 1.92 mmol) and imidazole (327 mg, 4.80 mmol) in dichloromethane (15 cm3). A thick precipitate formed immediately. After 1 h the mixture was poured into water (50 cm3). The layers were shaken and separated and then the aqueous phase was further extracted with dichloromethane (2×50 cm3). The combined extracts were washed with brine (50 cm3) then dried (Na2SO4) and evaporated to a pale yellow oil. This was taken up in 20% ethyl acetate in petroleum ether and filtered through a plug of silica. Evaporation of the filtrate gave the title compound as a pale yellow oil (936 mg) which was used immediately for the next step.

Workup

  1. customA thick precipitate formed immediately
  2. customseparated
  3. extractionthe aqueous phase was further extracted with dichloromethane (2×50 cm3)
  4. washThe combined extracts were washed with brine (50 cm3)
  5. dry with materialthen dried (Na2SO4)
  6. customevaporated to a pale yellow oil
  7. filtrationfiltered through a plug of silica
  8. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-fa136802b95849b1b9720196a1d9fd49
Source dataset
uspto-grants-2009_09
Patent number
US07589170B1

Reaction notes

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