1-Cyclopentyl-2-propen-1-ol → HCID 68866580, compound

HRID 858780Notes

Reaction equation

HRID 858780 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[C:4]([F:12])[CH:3]=1.[CH:13]1([CH:18]([OH:21])[CH:19]=[CH2:20])[CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[CH:13]1([C:18](=[O:21])[CH2:19][CH2:20][C:2]2[CH:11]=[CH:10][C:5]([O:6][CH2:7][C:8]#[N:9])=[C:4]([F:12])[CH:3]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 1451331-Cyclopentyl-2-propen-1-olHCID 516892Sodium BicarbonateHCID 43084322HCID 43084322, compound

Product 1

HCID 68866580HCID 68866580, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of (4-bromo-2-fluorophenoxy)acetonitrile (2.5 g, 10.8 mmol), 1-Cyclopentyl-2-propen-1-ol (2.0 g, 16.2 mmol), dichlorobis (triphenylphosphine) palladium (II) (151 mg, 0.22 mmol), and sodium bicarbonate (1.08 g, 12.9 mmol) in N-methylpyrrolidinone (20 mL) was heated to 140° C. under N2 for 5 hours. The reaction mixture was partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to a black oil. The oil was purified by flash column chromatography (Hexanes to 10% EtOAc in hexanes) to give the desired product (2.7 g, 93%). 1H NMR (CDCl3): δ 1.52–1.83 (m, 8H), 2.75 (m, 2H), 2.85 (m, 3H), 4.80 (s, 2H), 6.92–7.06 (m, 3H).

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a black oil
  5. customThe oil was purified by flash column chromatography (Hexanes to 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8834134a3af544e1878df7d64b6e2710
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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