Triethylamine → methyl (5-(3-hydroxyphenyl)-2H-tetrazol-2-yl)acetate

HRID 1945277Notes

Reaction equation

HRID 1945277 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:7]=[C:8]([OH:12])[CH:9]=[CH:10][CH:11]=1.CCN(CC)CC.Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CC#N>[CH3:25][O:24][C:22](=[O:23])[CH2:21][N:3]1[N:2]=[N:1][C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([OH:12])[CH:7]=2)=[N:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 134557633-(2H-Tetrazol-5-yl)phenol

Product 1

HCID 58482535methyl (5-(3-hydroxyphenyl)-2H-tetrazol-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(2H-tetrazol-5-yl)phenol (250.8 mg, 1.547 mmol) in MeCN (10 mL) at rt was added Et3N (0.237 mL, 1.701 mmol) followed by methyl bromoacetate (260 mg, 1.701 mmol). The reaction was stirred at rt for 16 h. Volatiles were removed. Chromatography over silica eluting with 30-60% EtOAc/hexanes afforded the title compound as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.75 (d, 1H, J=7.5 Hz), 7.69 (s, 1H), 7.39 (t, 1H, J=8.0 Hz), 7.01 (dd, 1H, J=8.0, 2.3 Hz), 5.53 (bs, 1H), 5.50 (s, 2H), 3.86 (s, 3H).

Workup

  1. customVolatiles were removed

Sources & evidence

ORD record
ord-8446105c835749cb9504f11a3893e15b
Source dataset
uspto-grants-2013_03
Patent number
US08394969B2

Reaction notes

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