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 → 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-butan-2-ol

HRID 546854Notes

Reaction equation

HRID 546854 reaction equation
[CH2:1]([C:3]([C:22]1[CH:27]=[CH:26][C:25]([C:28]#[C:29][C:30]([C:36]([F:39])([F:38])[F:37])([OH:35])[C:31]([F:34])([F:33])[F:32])=[C:24]([CH3:40])[CH:23]=1)([C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]2)=[C:8]([CH3:21])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[H][H]>CO.[C].[Pd]>[CH2:1]([C:3]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([C:31]([F:34])([F:32])[F:33])([OH:35])[C:36]([F:38])([F:37])[F:39])=[C:24]([CH3:40])[CH:23]=1)([C:6]1[CH:11]=[CH:10][C:9]([B:12]2[O:16][C:15]([CH3:17])([CH3:18])[C:14]([CH3:19])([CH3:20])[O:13]2)=[C:8]([CH3:21])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

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-olHCID 178418361HCID 178418361, compound

Product 1

HCID 577090734-(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-butan-2-olYield 94%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% palladium-carbon (50 mg) was added to a solution of 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 (Example 27-(1); 142 mg, 0.249 mmol) in methanol (6 mL), and the mixture was stirred in a hydrogen atmosphere at room temperature for five hours. Then, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure to give the target product as a colorless oil (134 mg, 94%).

Workup

  1. filtrationThen, the reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-10ebd83d907c4706b82596094863620c
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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