Triethylamine → 1-(Methanesulfonyloxymethyl)-3-(5-methyltetrazol-1-yl)-5-(trifluoromethyl)benzene

HRID 355375Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[N:11]([C:12]2[CH:13]=[C:14]([CH2:22][OH:23])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=2)[N:10]=[N:9][N:8]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:23][CH2:22][C:14]1[CH:15]=[C:16]([C:18]([F:19])([F:21])[F:20])[CH:17]=[C:12]([N:11]2[C:7]([CH3:6])=[N:8][N:9]=[N:10]2)[CH:13]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: -30 °C

Procedure

Methanesulfonyl chloride (0.26 ml, 0.39 g, 3.4 mmol) was added dropwise to a stirred, cooled (-30° C.) solution of 3-(5-methyltetrazol-1-yl)-5-(trifluoromethyl)phenylmethanol (725 mg, 2.8 mmol) and triethylamine (0.59 ml, 0.43 g, 4.2 mmol) in dichloromethane (15 ml). The mixture was stirred at -30° C. for 45 minutes, diluted with dichloromethane (20 ml), washed with aqueous citric acid (10%, 20 ml) and saturated aqueous sodium hydrogen carbonate (20 ml), dried (MgSO4) and the solvent was evaporated under reduced pressure to give 1-(methanesulfonyloxymethyl)-3-(5-methyltetrazol-1-yl)-5-(trifluoromethyl)benzene as a yellow oil (877 mg, 93%), 1H (CDCl3) δ 7.86 (1H, s), 7.81 (2H, s), 5.38 (2H, s), 3.14 (3H, s), and 2.69 (3H, s).

Workup

washwashed with aqueous citric acid (10%, 20 ml) and saturated aqueous sodium hydrogen carbonate (20 ml)
dry with materialdried (MgSO4)
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-5558cf3524b64ef6bd6cd5f93ca0caf5
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05830892

Reaction notes

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