Diethyl Ether → HCID 178519555, compound

HRID 591794Notes

Reaction equation

HRID 591794 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.C[O:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]2[NH:26][N:25]=[N:24][N:23]=2)=[CH:17][CH:16]=1>C1COCC1>[NH:26]1[C:22]([CH2:21][C:18]2[CH:19]=[CH:20][C:15]([CH2:14][OH:13])=[CH:16][CH:17]=2)=[N:23][N:24]=[N:25]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 178497695HCID 178497695, compound

Product 1

HCID 178519555HCID 178519555, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (0.142 g, 3.75 mmol) was taken in a dry, three-necked flask, fitted with a reflux condenser. Anhydrous ether (10 mL) was added. A solution of methyl-4-(1H-tetrazol-5-ylmethyl)benzoate (0.654 g, 3.0 mmol) in anhydrous THF (5 mL) was added dropwise. After the addition was complete, the mixture was heated to reflux for 2 hours. Then, the reaction mixture was cooled to 0° C. and quenched by cautious addition of water (10 mL) and 15% sodium hydroxide solution (10 mL). The reaction mixture was stirred for 30 minutes and then allowed to warm to room temperature. The aqueous phase was acidified to pH 4 and left for 2 days. A white precipitate was formed and filtered off, washed with water, and dried under vacuum, to give [4-(1H-tetrazol-5-ylmethyl)-phenyl]-methanol as a white solid. Yield: 0.290 g (51%).

Workup

  1. customfitted with a reflux condenser
  2. additionAfter the addition
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 2 hours
  5. customquenched by cautious addition of water (10 mL) and 15% sodium hydroxide solution (10 mL)
  6. temperatureto warm to room temperature
  7. waitleft for 2 days
  8. customA white precipitate was formed
  9. filtrationfiltered off
  10. washwashed with water
  11. customdried under vacuum

Sources & evidence

ORD record
ord-a15f95f1a81742e7b72c3040073bfb2b
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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