Ethyl Acetate → HCID 86704528, compound

HRID 633435Notes

Reaction equation

HRID 633435 reaction equation
[CH:1]1([C:4]2[N:8]([C:9]3[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=3F)[N:7]=[N:6][N:5]=2)[CH2:3][CH2:2]1.[Si:19]([O:26][CH2:27][CH2:28][OH:29])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O>[Si:19]([O:26][CH2:27][CH2:28][O:29][C:10]1[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=1[N:8]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][N:6]=[N:7]1)([C:22]([CH3:24])([CH3:25])[CH3:23])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 111376652-(tert-Butyl(dimethyl)silyl)oxyethanolHCID 86704529HCID 86704529, compound

Product 1

HCID 86704528HCID 86704528, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-cyclopropyl-1-(2-fluoro-5-nitrophenyl)-1H-tetrazole (112 mg, 0.45 mmol), 2-((tert-butyldimethylsilyl)oxy)ethan-1-ol (159 mg, 0.9 mmol) and Cs2CO3 (325 mg, 1.0 mmol) in DMF (3 mL) was heated to 50° C. and stirred for 4 hr. The reaction was cooled and then poured in to EtOAc (30 mL) and H2O (20 mL). The aqueous and organic layers were partitioned and the aqueous was extracted with EtOAc (2×20 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was dry-loaded on to silica gel and purified by column chromatography on silica gel using EtOAc/heptane (4:6 to 1:0) to give the desired product (23 mg, 13% yield), followed by the desired product as de-silylated material, 2-(2-(5-cyclopropyl-1H-tetrazol-1-yl)-4-nitrophenoxy)ethan-1-ol (82 mg, 63%). Both products were taken to the final desired compound.

Workup

  1. temperatureThe reaction was cooled
  2. customThe aqueous and organic layers were partitioned
  3. extractionthe aqueous was extracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customto leave a crude residue
  8. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-5a6ee1a227394334b2e6297ee64076ab
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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