Citric Acid → HCID 87225321, compound

HRID 1454510Notes

Reaction equation

HRID 1454510 reaction equation
[Br:1][C:2]1[C:3]([OH:15])=[C:4]([CH:7]=[C:8]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:9]=1)[CH:5]=[O:6].C(N(C(C)C)CC)(C)C.[CH3:25][O:26][CH2:27][CH2:28][O:29][CH2:30]Cl.C(O)(=O)C[C:34](CC(O)=O)(C(O)=O)[OH:35].[C:45]([O:48][CH2:49][CH3:50])(=O)C>ClCCl>[Br:1][C:2]1[C:3]([O:15][CH2:34][O:35][CH2:50][CH2:49][O:48][CH3:45])=[C:4]([CH:7]=[C:8]([C:10]2[N:14]([CH2:25][O:26][CH2:27][CH2:28][O:29][CH3:30])[N:13]=[N:12][N:11]=2)[CH:9]=1)[CH:5]=[O:6]

Participants

7

Reactant 5

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 178519390HCID 178519390, compound

Product 1

HCID 87225321HCID 87225321, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-bromo-2-hydroxy-5-(1H-tetrazol-5-yl)benzaldehyde in dichloromethane (25 mL) was treated with diisopropylethylamine (1.2 mL, 6.4 mmol) and 2-methoxyethoxymethyl chloride (0.72 mL, 6.4 mmol) under a stream of nitrogen and the mixture was stirred at room temperature for 2 hours. Workup involved rotovaping off most of the dichloromethane, followed by usual extractive workup with ethyl acetate and 5% aqueous citric acid. Collection and drying of the organic extracts gave a regioisomeric mixtures of 3-bromo-2-(methoxyethoxymethoxy)-5-(1-(methoxyethoxymethyl)-1H-tetrazol-5-yl)benzaldehyde (0.93 g) as an oil.

Workup

  1. customCollection
  2. customdrying of the organic extracts

Sources & evidence

ORD record
ord-4f1a874000124ca9a1c59904f97a2171
Source dataset
uspto-grants-2009_01
Patent number
US07479502B2

Reaction notes

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