Hydrochloric Acid → 5,6-Difluoro-3-pentyl-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene

HRID 1873312Notes

Reaction equation

HRID 1873312 reaction equation
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[CH:4][C:3]=1[O:18][CH:19]([CH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]1)[C:20]#[CH:21].[F-].[K+].O.Cl>C(N(CC)C1C=CC=CC=1)C>[F:12][C:11]1[C:2]([F:1])=[C:3]2[C:4]([CH:21]=[CH:20][CH:19]([CH:22]3[CH2:23][CH2:24][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:26][CH2:27]3)[O:18]2)=[C:5]2[CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9][C:10]=12

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 522689Potassium FluorideHCID 581519077,8-Difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman

Product 1

HCID 581519145,6-Difluoro-3-pentyl-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Procedure

9.7 g (23.2 mmol) of 7,8-difluoro-2-pentyl-6-[1-(4-propylcyclohexyl)prop-2-ynyloxy]chroman are heated at 200° C. for 6 h together with 2.7 g (46.5 mmol) of potassium fluoride in 75 ml of N,N-diethylaniline. After cooling, water is added, and the mixture is acidified using 25% hydrochloric acid. The batch is extracted with MTBE, and the organic phase is washed with saturated sodium chloride solution. The solution is dried using sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography (SiO2, 1-chlorobutane:pentane=4:1), giving 5,6-difluoro-3-pentyl-8-(4-propylcyclohexyl)-1,2,3,8-tetrahydropyrano[3,2-f]chromene as a pale-brown oil.

Workup

  1. temperatureAfter cooling
  2. extractionThe batch is extracted with MTBE
  3. washthe organic phase is washed with saturated sodium chloride solution
  4. customThe solution is dried
  5. customevaporated to dryness
  6. customThe crude product is purified by column chromatography (SiO2, 1-chlorobutane:pentane=4:1)

Sources & evidence

ORD record
ord-89592df4ae1148a2b2851dd0939ee196
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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