Water → 2-Cyclopentoxy-5-tetrazol-1-ylbenzaldehyde

HRID 376267Notes

Reaction equation

HRID 376267 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][N:12]=[N:11]2)=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:21]1(Br)[CH2:25][CH2:24][CH2:23][CH2:22]1.O>CN(C)C=O>[CH:21]1([O:1][C:2]2[CH:9]=[CH:8][C:7]([N:10]3[CH:14]=[N:13][N:12]=[N:11]3)=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 108453442-Hydroxy-5-tetrazol-1-yl-benzaldehyde

Product 1

HCID 193617862-Cyclopentoxy-5-tetrazol-1-ylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-5tetrazol-1-yl-benzaldehyde (500 mg) and potassium carbonate (431 mg) in dimethylformamide (5 ml) at 20° was treated with cyclopentyl bromide (0.33 ml). After 24 h water (20 ml) was added and the mixture extracted with ethyl acetate (2×25 ml). The organics were washed with water (25 ml) and brine (25 ml) and dried (Na2SO4). Evaporation gave a yellow solid which was purified by FCC (ethyl acetate/cyclohexane (2:1)) to give the title compound, as a yellow solid (334 mg).

Workup

  1. extractionthe mixture extracted with ethyl acetate (2×25 ml)
  2. washThe organics were washed with water (25 ml) and brine (25 ml)
  3. dry with materialdried (Na2SO4)
  4. customEvaporation
  5. customgave a yellow solid which
  6. customwas purified by FCC (ethyl acetate/cyclohexane (2:1))

Sources & evidence

ORD record
ord-f3cadf8ca23940e79733b9ddbce6cae0
Source dataset
uspto-grants-2000_02
Patent number
US06020346

Reaction notes

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