Water → HCID 49834378, compound

HRID 1627063Notes

Reaction equation

HRID 1627063 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:7]=1[C:21]([F:24])([F:23])[F:22].[C:26]1(=[O:31])[CH2:30][CH2:29][CH:28]=[CH:27]1.[Li+].[OH-].O>O.C(COC)OC>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:28]2[CH2:29][CH2:30][C:26](=[O:31])[CH2:27]2)=[CH:8][C:7]=1[C:21]([F:22])([F:23])[F:24]

Participants

6

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 135882-Cyclopenten-1-oneHCID 49834377HCID 49834377, compound

Product 1

HCID 49834378HCID 49834378, compound

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-trifluoromethyl-phenyl]-propionic acid methyl ester (preparation 2) (4.6 mmol) and [(1,4-hydroquinone)-rhodium(COD)]BF4 (Son et al., J. Am. Chem. Soc. 2005, 127, 12238) (2 mol %) in water/dimethoxyethane (1:1, 20 mL, degassed) was added 2-cyclopenten-1-one (4.6 mmol) and LiOH (8 mol %). The mixture was warmed to 50° C. and stirred overnight. Additional water was added, and the mixture was extracted with dichloromethane. The organic phase was separated, dried and concentrated in vacuo to afford the title compound as a brown oil. 1H NMR (300 MHz, DMSO) δ 7.72-7.56 (m, 2H), 7.54-7.39 (m, 1H), 3.62 (s, 3H), 3.53-3.36 (m, 1H), 3.08-2.95 (m, 2H), 2.70-2.47 (m, 3H), 2.43-2.21 (m, 4H), 2.02-1.83 (m, 1H).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. customThe organic phase was separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-58b46423fb784a959aa8797df6494b1b
Source dataset
uspto-grants-2014_07
Patent number
US08785494B2

Reaction notes

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