Ethanol → HCID 178518976, compound

HRID 386393Notes

Reaction equation

HRID 386393 reaction equation
[OH-].[Na+].[C:3]1([N:13]2[C:17](S)=[N:16][N:15]=[N:14]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.C([OH:21])C.C1OC1C>O>[C:3]1([N:13]2[C:17]([OH:21])=[N:16][N:15]=[N:14]2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6378Propylene OxideHCID 14798Sodium HydroxideHCID 178527985HCID 178527985, compound

Product 1

HCID 178518976HCID 178518976, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of sodium hydroxide (114 mg, 2.9 mmol) in water (0.5 mL) was added 1-(naphthalen-1-yl)-1H-tetrazole-5-thiol (490 mg, 2.2 mmol) and ethanol (5 mL). The reaction mixture was then cooled to 0° C., propylene oxide (168 mg, 2.9 mmol) added dropwise and the mixture stirred at 0° C. for 30 minutes and then room temperature for 5 hours. The mixture was taken up and washed with ethyl acetate. The aqueous layer was acidified with aqueous HCl solution (1N) and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to give pure 1-(naphthalen-1-yl)-1H-tetrazol-5-ol (420 mg, 90%).

Workup

  1. waitroom temperature for 5 hours
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf0fc4a907384e639b8a0ce9ae008862
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

Loading…