1-Hexanol → HCID 23249444, compound

HRID 1391863Notes

Reaction equation

HRID 1391863 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[F:10][C:11]1[C:16]([CH:17]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[S:18]([C:21]([F:24])([F:23])[F:22])(=[O:20])=[O:19])=[C:15]([F:32])[C:14]([F:33])=[C:13](F)[C:12]=1[F:35].O.Cl>N1C=CC=CC=1>[CH2:1]([O:7][C:13]1[C:12]([F:35])=[C:11]([F:10])[C:16]([CH:17]([S:18]([C:21]([F:24])([F:22])[F:23])(=[O:19])=[O:20])[S:25]([C:28]([F:29])([F:30])[F:31])(=[O:26])=[O:27])=[C:15]([F:32])[C:14]=1[F:33])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 81031-HexanolHCID 24758Sodium hydrideHCID 102039861-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzeneHCID 21885828Hydrate;hydrochloride

Product 1

HCID 23249444HCID 23249444, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-20 °C

Procedure

Hexanol (1.5 mL, 12 mmol) was added to a pyridine (10 mL) solution dissolved with 60% sodium hydride containing mineral oil (0.56 g, 14 mmol) at 0° C., and the resultant solution was stirred for 1 hour at room temperature. After the solution was cooled to −20° C., pentafluorophenylbis(triflyl)methane (0.89 g, 2 mmol) was added. The reaction solution was stirred at −20° C. for 5 hours. After the reaction, the solution was acidified with 4 M hydrochloric acid water, and was extracted with diethylether. After drying with magnesium sulfate, the solution was filtrated, and the solvent was removed under reduced pressure. The crude product was purified by sublimation (0.2 to 0.3 torr, 65° C.), and 4-hexanoxy-2,3,5, 6-tetrafluorophenylbis(triflyl)methane was obtained at 99% yield (1.02 g, 1.98 mmol). 1H NMR (CDCl3, 300 MHz) δ 0.91 (t, J=7.1 Hz, 3H), 1.32 to 1.37 (m, 4H), 1.43 to 1.51 (m, 2H), 1.83 (quintet, J=6.8 Hz, 2H), 4.44 (t, J=6.8 Hz, 2H), 6.19 (s, 1H); 19F NMR (CDCl3, 282 MHz) δ−75.35 (s, 6F, 2CF3), −130.64 (dt, J=9.9, 21.2 Hz, 1F), −143.16 (br, 1F), −155.31 (d, J=21.2 Hz, 1F).

Workup

  1. customAfter the reaction
  2. extractionwas extracted with diethylether
  3. dry with materialAfter drying with magnesium sulfate
  4. filtrationthe solution was filtrated
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by sublimation (0.2 to 0.3 torr, 65° C.)

Sources & evidence

ORD record
ord-07e92d5eb7ae4a6dbdc62a576b992634
Source dataset
uspto-grants-2008_03
Patent number
US07339082B2

Reaction notes

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