Imidazole → 2-(1,1-Dimethyl-3-trifluoromethyl-3-trimethylsilanyloxyhex-5-ynyl)benzoic acid

HRID 2387312Notes

Reaction equation

HRID 2387312 reaction equation
[OH:1][C:2]([C:19]([F:22])([F:21])[F:20])([CH2:16][C:17]#[CH:18])[CH2:3][C:4]([C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([CH3:6])[CH3:5].N1C=CN=C1.Cl[Si:29]([CH3:32])([CH3:31])[CH3:30]>CN(C=O)C.C(OCC)C>[CH3:6][C:4]([C:7]1[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10])([CH3:5])[CH2:3][C:2]([C:19]([F:20])([F:21])[F:22])([O:1][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH2:16][C:17]#[CH:18]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 580261462-(3-Hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzoic acid

Product 1

HCID 580261432-(1,1-Dimethyl-3-trifluoromethyl-3-trimethylsilanyloxyhex-5-ynyl)benzoic acidYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-hydroxy-1,1-dimethyl-3-trifluoromethylhex-5-ynyl)benzoic acid (345 mg, 1.10 mmol) and imidazole (374 mg, 5.49 mmol) in 1 mL of DMF was added chlorotrimethylsilane (0.42 mL, 3.29 mmol). The reaction mixture was stirred for 2 hours then diluted with 75 mL of diethyl ether, washed with two 50 mL portions of 1M aqueous HCl, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2-(1,1-dimethyl-3-trifluoromethyl-3-trimethylsilanyloxy-hex-5-ynyl)benzoic acid (424 mg, 100%). MS (ES+) m/z 387 [M+H]+.

Workup

  1. washwashed with two 50 mL portions of 1M aqueous HCl
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ee7186fc55a44a68dd937d2ef6f09f9
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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