Water → (2,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate

HRID 1583574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1583574
[F:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([F:10])[C:5]([F:11])=[C:4]([F:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[F:26][C:27]([F:37])=[CH:28][C@H:29]1[C@H:31]([C:32](Cl)=[O:33])[C:30]1([CH3:36])[CH3:35].O>C(OCC)C>[F:26][C:27]([F:37])=[CH:28][C@H:29]1[C@H:31]([C:32]([O:9][CH2:8][C:7]2[C:2]([F:1])=[C:3]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:4]([F:12])=[C:5]([F:11])[C:6]=2[F:10])=[O:33])[C:30]1([CH3:35])[CH3:36]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 202592392,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-methanolHCID 86740007trans-3-(2,2-Difluoroethenyl)-2,2-dimethylcyclopropanecarbonylchloride

Produkt 1

HCID 86740509(2,4,5,6-Tetrafluoro[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 0.97 g (3.8 mmole) of 2,4,5,6-tetrafluoro[1,1'-biphenyl]-3-methanol and 1 ml of dry triethylamine in 8 ml of dry diethyl ether was added 4 ml of a dry diethyl ether solution of trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (0.95 mmole/ml). The resultant mixture was stirred at room temperature for approximately 18 hours, then poured into 50 ml of water. The organic phase was separated, washed with a 5% aqueous sodium bicarbonate solution followed by a water wash, then dried over anhydrous magnesium sulfate. The organic phase was filtered, and the filtrate evaporated under reduced pressure to give an oil. The oil was purified by column chromatography on silica gel, eluted with ethyl acetate:hexanes (10:90), to yield 0.92 g of (2,4,5,6-tetrafluoro[1,1'-biphenyl]-3-yl)methyl trans-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropanecarboxylate as a solid (m.p. 69°-72° C.).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with a 5% aqueous sodium bicarbonate solution
  3. washwash
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe organic phase was filtered
  6. customthe filtrate evaporated under reduced pressure
  7. customto give an oil
  8. customThe oil was purified by column chromatography on silica gel
  9. washeluted with ethyl acetate:hexanes (10:90)

Quellen und Nachweise

ORD-Eintrag
ord-4bf454ccfcf848c3a6f9bed47b9f5e7a
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04552892

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