Potassium Hydroxide → HCID 86755181, compound

HRID 382451Notes

Reaction equation

HRID 382451 reaction equation
[O:1]1[C@H:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=[CH2:9])[CH2:2]1.[F:10][C:11]([F:33])([F:32])[O:12][C:13]([F:31])([O:18][C:19]([F:30])([O:24][C:25]([F:29])([F:28])[CH2:26][OH:27])[C:20]([F:23])([F:22])[F:21])[C:14]([F:17])([F:16])[F:15].ClC[C@H](O)CCCCC=C.[OH-].[K+]>O.COCCOC>[F:10][C:11]([F:32])([F:33])[O:12][C:13]([F:31])([O:18][C:19]([F:30])([O:24][C:25]([F:29])([F:28])[CH2:26][O:27][C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([OH:1])[CH3:2])=[CH2:9])[C:20]([F:22])([F:21])[F:23])[C:14]([F:17])([F:16])[F:15]

Participants

7

Reactant 4

HCID 14797Potassium Hydroxide2×HCID 6999067(2R)-2-hex-5-enyloxiraneHCID 21967268(2R)-1-Chloro-7-octen-2-olHCID 86755182HCID 86755182, compound2×

Product 1

HCID 86755181HCID 86755181, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
45 °C

Procedure

This chlorohydrin was converted in situ to (R)-1,2-epoxy-7-octene and reacted with 2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol using the following procedure: (R)-8-chloro-7-hydroxy-oct-1-ene (100 g, 0.61 mol), aqueous potassium hydroxide (45 mL of 45 wt. %), 2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethanol (291 g, 0.733 mol), Adogen™ 464 (60 g), and 1,2-dimethoxyethane (60 mL) were added to a one liter flask fitted with a mechanical stirrer, an addition funnel, a reflux condenser, and a thermometer. The resulting solution was stirred for one hour at 45° C. and then warmed to 60° C., at which time aqueous potassium hydroxide (70 mL of 45 wt %) was added dropwise. This solution was heated for 2 hours at 60° C. and then at 70° C. for 8 hours. Water (300 mL) was added, and the resulting organic phase was separated and washed with 7 weight % HCl (300 mL). The organic phase was again separated and was concentrated under reduced pressure (25 torr). The resulting crude product was then purified by silica gel chromatography using toluene as eluent to give 268 g of (R)-8-(2-(2-(2-(trifluoromethoxy(tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-7-hydroxyoct-1-ene.

Workup

  1. customfitted with a mechanical stirrer, an addition funnel, a reflux condenser
  2. additionwas added dropwise
  3. temperatureThis solution was heated for 2 hours at 60° C.
  4. waitat 70° C. for 8 hours
  5. customthe resulting organic phase was separated
  6. washwashed with 7 weight % HCl (300 mL)
  7. customThe organic phase was again separated
  8. concentrationwas concentrated under reduced pressure (25 torr)
  9. customThe resulting crude product was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-2a7f5c26aaf644a9abb729eed8f236fb
Source dataset
uspto-grants-2001_10
Patent number
US06309561B1

Reaction notes

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