Pentane → HCID 18400181, compound

HRID 1735446Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[Li]C(C)(C)C.CCCCC.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28](=[O:32])[CH2:29][CH2:30][CH:31]=2)=[CH:23][CH:22]=1>CCOCC>[CH3:9][S:8][C:5]1[CH:6]=[CH:7][C:2]([C:28]2([OH:32])[CH2:29][CH2:30][CH:31]=[C:27]2[C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3.86 g (19 mmol) of 4-bromothioanisole in 90 mL of Et2O cooled at -78° C., was added 22 mL of 1.7M solution of t-BuLi in pentane (38 mmol) dropwise. The reaction mixture was stirred for 15 min at -78° C. and a solution of 2.23 g of 2-(4-Fluorophenyl)-2-cyclopenten-1-one in 10 mL of Et2O was added. After stirring for 15 min at -78° C., the reaction mixture was warmed to 0° C., and quenched with 50 mL of sat. NH4Cl. The product was extracted with 100 mL EtOAc, dried over Na2SO4, and purified by flash chromatography, eluted with 4:1 hexane/EtOAc to give 3.4 g of the desired product. 1H NMR (CDCl3) δ2.12 (1H, s), 2.34 (2H, m), 2.44 (3H, s), 2.45-2.52 (1H, m), 2.56-2.65 (1H, m), 6.37 (1H, m), 6.84 (2H, J=8.7 Hz, t), 7.17 (2H, J=8.3 Hz, d), 7.24-7.33 (4H, m).

Workup

stirringAfter stirring for 15 min at -78° C.
temperaturethe reaction mixture was warmed to 0° C.
customquenched with 50 mL of sat. NH4Cl
extractionThe product was extracted with 100 mL EtOAc
dry with materialdried over Na2SO4
custompurified by flash chromatography
washeluted with 4:1 hexane/EtOAc

Sources & evidence

ORD record: ord-bafe431932cf4fb99474a4636bf117e9
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05536752

Reaction notes

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