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

HRID 859699Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4-bromo-2-chloro-1-methanesulfonyl-benzene (1.5 g, 5.6 mmol), 1-cyclopentyl-2-propen-1-ol (0.88 g, 6.96 mmol) and sodium acetate (0.57 g, 6.9 mmol) in DMAC (20 mL) was purged with N2 for 30 mins. Palladium (II) acetate (25 mg, 0.11 mmol) was added and the mixture was heated to 90° C. under N2 for 16 hours. The reaction mixture was partitioned between 1 N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to a brown oil. Purification by flash column chromatography (0% to 20% EtOAc in hexanes) gave the desired product (1.2 g, 69%). 1H NMR (300 MHz, CDCl3): δ 1.56–1.85 (br m, 8 H), 2.83 (m, 3 H), 2.96 (t, J=7.5 Hz, 2 H), 3.25 (s, 3 H), 7.29 (dd, J=8.1, 1.5 Hz, 1 H), 7.39 (d, J=1.5 Hz, 1 H), 8.04 (d, J=8.1 Hz, 1 H).

Workup

customwas purged with N2 for 30 mins
customThe reaction mixture was partitioned between 1 N HCl and EtOAc
washThe organic layers were washed with saturated NaHCO3, brine
dry with materialdried over Na2SO4
concentrationconcentrated to a brown oil
customPurification by flash column chromatography (0% to 20% EtOAc in hexanes)

Sources & evidence

ORD record: ord-4de18c506c484269841f969f57a61f74
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151105B2

Reaction notes

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