6-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman → 5,6-Difluoro-3-pentyl-8-propyl-1,2,3,8-tetrahydropyrano[3,2-f]-chromene

HRID 1873314Notes

Reaction equation

HRID 1873314 reaction equation
[C:1]([CH:3]([O:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([F:19])[C:17]=1[F:18])[O:14][CH:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:11]2)[CH2:4][CH2:5][CH3:6])#[CH:2]>C(N(CC)C1C=CC=CC=1)C.CC(OC)(C)C>[F:19][C:16]1[C:17]([F:18])=[C:8]2[C:9]([CH:2]=[CH:1][CH:3]([CH2:4][CH2:5][CH3:6])[O:7]2)=[C:10]2[CH2:11][CH2:12][CH:13]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[O:14][C:15]=12

Participants

4

Reactant 1

HCID 581519006-(1-Ethynylbutoxy)-7,8-difluoro-2-pentylchroman

Product 1

HCID 581519185,6-Difluoro-3-pentyl-8-propyl-1,2,3,8-tetrahydropyrano[3,2-f]-chromene

Reagents, catalysts & solvents 2

HCID 7061N,N-DiethylanilineSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

9.0 g (26.8 mmol) of 6-(1-ethynylbutoxy)-7,8-difluoro-2-pentylchroman are heated at 205° C. for 3 h in 90 ml of N,N-diethylaniline. The batch is diluted with MTBE and washed a number of times with 3 N HCl. The organic phase is dried using sodium sulfate and evaporated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1), giving 5,6-difluoro-3-pentyl-8-propyl-1,2,3,8-tetrahydropyrano[3,2-f]-chromene as a pale-brown oil.

Workup

  1. washwashed a number of times with 3 N HCl
  2. customThe organic phase is dried
  3. customevaporated to dryness
  4. customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1)

Sources & evidence

ORD record
ord-5ab23ce4abd542ec92b11f8b31310418
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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