Water → HCID 66696588, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][CH:15]=[N:14][C:13]=2[CH3:17])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:28]C(Cl)(Cl)C(Cl)(Cl)Cl.O>O1CCCC1.C(OCC)(=O)C.CCCCCC>[Cl:28][C:15]1[O:16][C:12]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:11])[F:10])=[C:2]([F:1])[CH:3]=2)=[C:13]([CH3:17])[N:14]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A solution of Example 1B (1.01 g, 4.12 mmol) in tetrahydrofuran (20 mL) was cooled to −78° C., then lithium bis(trimethylsilyl)amide (1M in tetrahydrofuran, 4.6 mL, 4.6 mmol) was added slowly. The reaction was allowed to stir at −78° C. for 20 minutes, and then hexachloroethane (1.95 g, 8.23 mmol) was added all at once. The reaction was allowed to warm to room temperature, and stir overnight. After this time, the reaction mixture was poured into water and extracted with ether. The extracts were dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on silica gel (eluant of 100% hexane, then gradient to 15% ethyl acetate-hexane) to yield the title compound as a white solid (780 mg, 68% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.91 (m, 1H), 7.66 (m, 2H), 2.42 (s, 3H).
Workup
- temperatureto warm to room temperature
- stirringstir overnight
- extractionextracted with ether
- dry with materialThe extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was chromatographed on silica gel (eluant of 100% hexane
Sources & evidence
- ORD record
- ord-45ea7d05c5cc450baf05d8b807de156b
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998993B2
Reaction notes
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