1-Cyclopentyl-2-propen-1-ol → HCID 58762532, compound

HRID 1453066Notes

Reaction equation

HRID 1453066 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[CH:12]1([CH:17]([OH:20])[CH:18]=[CH2:19])[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:12]1([C:17](=[O:20])[CH2:18][CH2:19][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([CH2:10][CH3:11])[CH:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 1451331-Cyclopentyl-2-propen-1-olHCID 516892Sodium BicarbonateHCID 133016024-Bromo-2-ethyl-1-methoxybenzene

Product 1

HCID 58762532HCID 58762532, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of bromide (1.3 g, 6.02 mmol, from step 1), 1-Cyclopentyl-2-propen-1-ol (1.14 g, 9.07 mmol), dichlorobis(triphenylphosphine)palladium (II) (85 mg, 0.12 mmol), sodium bicarbonate (0.61 g, 7.25 mmol) in N-methylpyrrolidinone (12 mL) was heated to 140° C. under N2 for 5 h. 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 brown oil. The oil was purifed by silica gel chromatography to give the title compound as a yellow oil (0.74 g, 47%). 1H NMR (CDCl3): δ ?1.17 (t, 3H, J=7.6 Hz), 1.54-1.80 (m, 9H), 1.17 (q, 2H, J=7.6 Hz), 2.73 (m, 2H), 2.84 (m, 2H), 3.80 (s, 3H), 6.75 (d, 1H, J=8.0 Hz), 6.97 (m, 2H).

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 brown oil

Sources & evidence

ORD record
ord-947f42e515c34f5c8698bb4500339625
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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