Citric Acid → 1-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-2-phenyl-ethane-1,2-diol

HRID 639773Notes

Reaction equation

HRID 639773 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10](C=CC3C=CC=CC=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:21](O)(=O)[CH2:22][C:23]([CH2:28][C:29]([OH:31])=O)([C:25](O)=O)O.[C:34](O)(C)(C)[CH3:35].C[N+]1([O-])CC[O:43]CC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:29]([OH:31])[CH:28]([C:23]3[CH:22]=[CH:21][CH:35]=[CH:34][CH:25]=3)[OH:43])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 684297582-(3-Chloro-phenyl)-5-styryl-2H-tetrazole

Product 1

HCID 594242241-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-2-phenyl-ethane-1,2-diolYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(3-Chloro-phenyl)-5-styryl-2H-tetrazole (127.0 mg, 0.446 mmol) was weighed into a vial and citric acid (171.35 mg, 0.892 mmol) was added followed by a 1:1 mixture of t-butanol and water (3 mL). Potassium osmate oxide hydrate (0.3 mg) was added followed by 4-methyl morpholine N-oxide (in 1.5 mL of water) and the reaction was allowed to stir overnight. The reaction was filtered and washed with water and 1M hydrochloric acid to yield the title compound as a beige solid (95.4 mg, 68%). 1H NMR (MeOD) δ (ppm): 8.086 (s, 1H); 8.012 (d of t, 1H); 7.584 (m, 2H); 7.252 (m, 5H); 5.148 (s, 2H).

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered
  3. washwashed with water and 1M hydrochloric acid

Sources & evidence

ORD record
ord-fc4059e5c5bd4a20928723f1e15559f2
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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