Methane → [4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetic acid

HRID 82315Notes

Reaction equation

HRID 82315 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12]2)[N:8]=[N:7]1)C.[OH-].[Na+].C.OS([O-])(=O)=O.[Na+]>O.CCOC(C)=O>[OH:16][C:11]1([C:9]2[N:8]=[N:7][N:6]([CH2:5][C:4]([OH:17])=[O:3])[CH:10]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 297MethaneHCID 14798Sodium HydroxideHCID 516919Sodium BisulfateHCID 70847803ethyl[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetate

Product 1

HCID 70817720[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetic acidYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]acetate (Preparation 293, 36.4 g, 151 mmol) in water (50 mL), was added a solution of NaOH (7.60 g, 190 mmol) in water (25 mL). The solution was refluxed with activated charcoal, filtered through Celite, and NaHSO4 (25.8 g, 190 mmol) added. EtOAc (50 mL) was added to the filtrate. The formed precipitate was separated by filtration, dissolved in EtOAc (100 mL), and the solution was filtered. The water layer was extracted with EtOAc (10×50 mL), and the combined extracts were evaporated to a volume of 100 mL. The precipitate was filtered, washed with ethyl acetate (2×50 mL), and concentrated under reduced pressure to afford the title compound as a colorless crystalline substance in 87% yield, 27.8 g. mp 124.0-126.0° C.; MS m/z 212 [M+H]+

Workup

  1. additionadded
  2. customThe formed precipitate was separated by filtration
  3. dissolutiondissolved in EtOAc (100 mL)
  4. filtrationthe solution was filtered
  5. extractionThe water layer was extracted with EtOAc (10×50 mL)
  6. customthe combined extracts were evaporated to a volume of 100 mL
  7. filtrationThe precipitate was filtered
  8. washwashed with ethyl acetate (2×50 mL)
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a59b45d7c7f344b6a961f07b3c1abe14
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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