1-Cyclopentyl-2-propen-1-ol → 3-(3-Chloro-5-ethyl-4-methoxy-phenyl)-1-cyclopentyl-propan-1-one

HRID 858771Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:11][CH3:12])[C:5]([O:9][CH3:10])=[C:6]([Cl:8])[CH:7]=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>[Cl:8][C:6]1[CH:7]=[C:2]([CH2:20][CH2:19][C:18]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:21])[CH:3]=[C:4]([CH2:11][CH3:12])[C:5]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 5-bromo-1-chloro-3-ethyl-2-methoxy-benzene (2 g, 8 mmol), 1-Cyclopentyl-2-propen-1-ol (1.3 g, 10.4 mmol), dichlorobis (triphenylphosphine) palladium (II) (110 mg, 0.16 mmol), and sodium bicarbonate (0.81 g, 9.6 mmol) in N-methylpyrrolidinone (15 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 black oil. The oil was purified by flash column chromatography (0% to 10% EtOAc in hexanes) to give the desired product (1.9 g, 82%). 1H NMR (400 MHz, CDCl3): δ 1.20 (t, J=7.6 Hz, 3 H), 1.53–1.81 (m, 8 H), 2.65 (q, J=7.6 Hz, 2 H), 2.74 (m, 2 H), 2.79–2.87 (m, 3 H), 3.81 (s, 3 H), 6.90 (s, 1 H), 7.03 (m, 1 H).

Workup

customThe reaction mixture was partitioned between 1N HCl and EtOAc
washThe organic layer was washed with saturated NaHCO3, brine
dry with materialdried over Na2SO4
concentrationconcentrated to black oil
customThe oil was purified by flash column chromatography (0% to 10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-69e5fced1e7d4ac09110b75612b901f1
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07148226B2

Reaction notes

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