Trifluoroacetic acid → 4-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-butyn-2-ol

HRID 546853Notes

Reaction equation

HRID 546853 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([C:10]([C:35]1[CH:40]=[CH:39][C:38]([B:41]2[O:45][C:44]([CH3:47])([CH3:46])[C:43]([CH3:49])([CH3:48])[O:42]2)=[C:37]([CH3:50])[CH:36]=1)([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([O:30]COC)([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[C:15]([CH3:34])[CH:14]=1)[CH2:11][CH3:12])[CH3:9]>ClCCl>[CH2:8]([C:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:21]([C:22]([F:25])([F:23])[F:24])([OH:30])[C:26]([F:28])([F:27])[F:29])=[C:15]([CH3:34])[CH:14]=1)([C:35]1[CH:40]=[CH:39][C:38]([B:41]2[O:45][C:44]([CH3:46])([CH3:47])[C:43]([CH3:48])([CH3:49])[O:42]2)=[C:37]([CH3:50])[CH:36]=1)[CH2:11][CH3:12])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 577089482-(4-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 577092074-(4-{1-Ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-butyn-2-olYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.8 mL) was added to a solution of 2-(4-{1-ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-1-butynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 25-(4); 284 mg, 0.464 mmol) in dichloromethane (4 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for six hours. Then, the reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 70:30) to give the target product as a colorless oil (142 mg, 54%).

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-9477e6b3dcf64178be98fa064bb7aa15
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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