Imidazole → HCID 58169522, compound

HRID 1484973Notes

Reaction equation

HRID 1484973 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]([C:9]1[S:10][C:11]([Br:14])=[CH:12][CH:13]=1)[OH:8])(=[O:3])[CH3:2].[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CN=C1.O>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][CH:7]([C:9]1[S:10][C:11]([Br:14])=[CH:12][CH:13]=1)[O:8][Si:19]([C:16]([CH3:18])([CH3:17])[CH3:15])([CH3:21])[CH3:20])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 581691293-(5-Bromothiophen-2-yl)-3-hydroxypropyl acetate

Product 1

HCID 58169522HCID 58169522, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5-bromothiophen-2-yl)-3-hydroxypropyl acetate (1.92 g, 6.9 mmol, 1.0 equiv.), TBDMSCl (1.24 g, 8.3 mmol, 1.2 eq) and 1H-imidazol (1.4 g, 20.7 mmol, 3.0 eq) in CH2Cl2 (50 mL) was stirred for 4 h at 60° C. Water was added and the reaction was extracted with EtOAc (3×200 ml). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to give a residue, which was purified by silica gel column chromatography (PE/EA=100:1 as eluant) to produce 3-(5-bromothiophen-2-yl)-3-(tert-butyldimethylsilyloxy)propyl acetate (2.6 g, 97.6%) as yellow oil. LC-MS (m/z): 393.1 [M+H]+;

Workup

  1. extractionthe reaction was extracted with EtOAc (3×200 ml)
  2. washThe combined organic phases were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue, which
  7. customwas purified by silica gel column chromatography (PE/EA=100:1 as eluant)

Sources & evidence

ORD record
ord-eec7a8c4707f4872b4305de47fc4374a
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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