Cesium fluoride → HCID 18679588, compound

HRID 1934541Notes

Reaction equation

C[Si](C)(C)[O:3][C:4]([C:6]1[O:7][CH:8]=[CH:9][CH:10]=1)=[CH2:5].[F-].[Cs+].[F:15][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])=[O:26])[CH:19]=[CH:20][C:21]=1[F:22]>CS(C)=O>[F:15][C:16]1[CH:17]=[C:18]([CH:23]([CH2:3][C:4]([C:6]2[O:7][CH:8]=[CH:9][CH:10]=2)=[O:5])[CH2:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[OH:33])=[O:26])[CH:19]=[CH:20][C:21]=1[F:22]

Participants

Conditions

Temperature: 70 °C

Procedure

1-Trimethylsilyloxy-1-(furan-2-yl)ethylene (7.0 mmol; prepared according to J. Chem. Soc., Perkin Trans. I 1989, 1585) and CsF (0.27 g, 1.76 mmol) were added to a suspension of 3-(3,4-difluorophenyl)-1-(2-hydroxyphenyl)-2-propen-1-one on Wang resin (2.0 g, 1.76 mmol) in dimethyl sulfoxide (30 mL). The reaction mixture was heated to 70° C. for 3 h and the reaction was quenched with 10% AcOH/CH2Cl2. The resin was filtered, washed with DMF (×2) and alternating MeOH and CH2Cl2 (×5), and dried under high vacuum overnight to give 3-(3,4-difluorophenyl)-5-(furan-2-yl)-1-(2-hydroxyphenyl)-1,5-pentanedione on Wang resin.

Workup

customthe reaction was quenched with 10% AcOH/CH2Cl2
filtrationThe resin was filtered
washwashed with DMF (×2)
customdried under high vacuum overnight

Sources & evidence

ORD record: ord-d0327ebfd554465b86bb37d0beda2869
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384060B1

Reaction notes

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