Imidazole → HCID 53821858, compound

HRID 733336Notes

Reaction equation

HRID 733336 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:26][C:27]1[CH:42]=[CH:41][C:30]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])=[CH:29][C:28]=1[OH:43])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CN=C1.O>ClCCl>[Si:1]([O:43][C:28]1[CH:29]=[C:30]([CH:41]=[CH:42][C:27]=1[O:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 54394841HCID 54394841, compound

Product 1

HCID 53821858HCID 53821858, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of tert-butyldiphenylsilyl chloride (850 mg, 3.09 mmol) in dichloromethane (10 cm3+5 cm3 rinse) was added to a stirred solution of benzyl 4-benzyloxy-3-hydroxybenzoate (827 mg, 2.47 mmol) and imidazole (421 mg, 6.18 mmol) in dichloromethane (15 cm3). After a few minutes a precipitate formed. The mixture was stirred overnight under an atmosphere of nitrogen, then was poured into water (50 cm3) The layers were shaken and separated, then the aqueous phase was further extracted with dichloromethane (2×50 cm3). The combined extracts were washed with brine (50 cm3) and evaporated to a pale yellow oil. This was filtered through a short silica column and eluted with 20% ethyl acetate in petroleum ether. Evaporation of the filtrate gave benzyl 3-(tert-butyldiphenylsilyloxy)-4-benzyloxybenzoate (1.646 g) as a very pale yellow oil, containing some tert-butyldiphenyl-silanol, which was used directly for the next step.

Workup

  1. customAfter a few minutes a precipitate formed
  2. stirringwere shaken
  3. customseparated
  4. extractionthe aqueous phase was further extracted with dichloromethane (2×50 cm3)
  5. washThe combined extracts were washed with brine (50 cm3)
  6. customevaporated to a pale yellow oil
  7. filtrationThis was filtered through a short silica column
  8. washeluted with 20% ethyl acetate in petroleum ether
  9. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-92c27181016f41b8808ec7e2a029655c
Source dataset
uspto-grants-2009_09
Patent number
US07589170B1

Reaction notes

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