Dimethylformamide → 6-(1H-Tetrazol-1-yl)-3,4-dihydronaphthalen-2(1H)-one

HRID 1519516Notes

Reaction equation

HRID 1519516 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[C:16](Cl)(=O)[C:17](Cl)=O.CN(C=O)C.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[N:1]1([C:6]2[CH:7]=[C:8]3[C:9](=[CH:10][CH:11]=2)[CH2:12][C:13](=[O:15])[CH2:17][CH2:16]3)[CH:5]=[N:4][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 841658(4-Tetrazol-1-yl-phenyl)-acetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 675172976-(1H-Tetrazol-1-yl)-3,4-dihydronaphthalen-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-(1H-tetrazol-1-yl)phenyl]acetic acid (0.50 g, 2.4 mmol) in DCM (10 mL) was added oxalyl chloride (0.37 g, 2.9 mmol) and a drop of DMF. The mixture was allowed to stir at RT for 2 hours. The solvent was removed under reduced pressure, and the residue was redissolved in DCM. The solution was cooled to 0° C. with an ice bath. To this solution was added aluminum chloride (0.98 g, 7.4 mmol) in small portions. Ethylene was then bubbled into the reaction via a long needle for 2 hours. LC showed formation of the desired product. The reaction was poured into ice and extracted with DCM. The extractions were combined, dried over sodium sulfate, adsorbed onto silica gel, and purified by MPLC (Hexane/EtOAc). The desired 6-(1H-tetrazol-1-yl)-3,4-dihydronaphthalen-2(1H)-one was collected as a off-white solid. LC-MS (IE, m/z): 215 [M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was redissolved in DCM
  3. temperatureThe solution was cooled to 0° C. with an ice bath
  4. customEthylene was then bubbled into the reaction via a long needle for 2 hours
  5. additionThe reaction was poured into ice
  6. extractionextracted with DCM
  7. extractionThe extractions
  8. dry with materialdried over sodium sulfate
  9. custompurified by MPLC (Hexane/EtOAc)
  10. customThe desired 6-(1H-tetrazol-1-yl)-3,4-dihydronaphthalen-2(1H)-one was collected as a off-white solid

Sources & evidence

ORD record
ord-8f97e5952703483f8fa028307e752bf8
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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