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 → 2-(4-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-butyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

HRID 546994Notes

Reaction equation

HRID 546994 reaction equation
[CH2:1]([C:3]([C:28]1[CH:33]=[CH:32][C:31]([B:34]2[O:38][C:37]([CH3:40])([CH3:39])[C:36]([CH3:42])([CH3:41])[O:35]2)=[C:30]([CH3:43])[CH:29]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]([O:23][CH2:24][O:25][CH3:26])([C:19]([F:22])([F:21])[F:20])[C:15]([F:18])([F:17])[F:16])=[C:8]([CH3:27])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[H][H]>CO.[C].[Pd]>[CH2:1]([C:3]([C:28]1[CH:33]=[CH:32][C:31]([B:34]2[O:35][C:36]([CH3:42])([CH3:41])[C:37]([CH3:39])([CH3:40])[O:38]2)=[C:30]([CH3:43])[CH:29]=1)([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]([O:23][CH2:24][O:25][CH3:26])([C:15]([F:18])([F:16])[F:17])[C:19]([F:22])([F:20])[F:21])=[C:8]([CH3:27])[CH:7]=1)[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 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]dioxaborolaneHCID 178418361HCID 178418361, compound

Product 1

HCID 577089172-(4-{1-Ethyl-1-[3-methyl-4-(4,4,4-trifluoro-3-methoxymethoxy-3-trifluoromethyl-butyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneYield 89%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Palladium carbon (10%, 53 mg) 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); 145.0 mg, 0.237 mmol) in methanol (6.5 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred in a hydrogen atmosphere at room temperature for four hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=30/1) to give the title compound (130 mg, 89%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=30/1)

Sources & evidence

ORD record
ord-5869dde595c04df2b96417672d17e648
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

Loading…