Hydrochloric Acid → 6,8-difluoro-3-[2-(6-fluoro-3-pentylchroman-7-yl)vinyl]-2H-chromene

HRID 2420650Notes

Reaction equation

HRID 2420650 reaction equation
[Br-].[F:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH2:13][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:9][CH2:8][CH:7]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:6]2.CC(C)([O-])C.[K+].[F:44][C:45]1[CH:46]=[C:47]2[C:52](=[C:53]([F:55])[CH:54]=1)[O:51][CH2:50][C:49]([CH:56]=O)=[CH:48]2.Cl>C1COCC1.O>[F:44][C:45]1[CH:46]=[C:47]2[C:52](=[C:53]([F:55])[CH:54]=1)[O:51][CH2:50][C:49]([CH:56]=[CH:13][C:12]1[CH:11]=[C:10]3[C:5]([CH2:6][CH:7]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:8][O:9]3)=[CH:4][C:3]=1[F:2])=[CH:48]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 592883586,8-difluoro-2H-chromene-3-carbaldehydeHCID 86641033(6-Fluoro-3-pentylchroman-7-ylmethyl)triphenylphosphonium bromide

Product 1

HCID 672154526,8-difluoro-3-[2-(6-fluoro-3-pentylchroman-7-yl)vinyl]-2H-chromene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

10.2 g (17.7 mmol) of (6-fluoro-3-pentylchroman-7-ylmethyl)triphenylphosphonium bromide are dissolved in 50 ml of THF, and 2.0 g (17.8 mmol) of potassium tert-butoxide are added with ice cooling. After 1 h, a solution of 6,8-difluoro-2H-chromene-3-carbaldehyde in 50 ml of THF is slowly added dropwise, and the batch is left to stir overnight at room temp. The solution is subsequently added to water, acidified using dil. hydrochloric acid and extracted three times with MTB ether. The combined org. phases are washed with sat. sodium chloride soln. and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is chromatographed on silica gel with heptane/toluene (1:1) and recrystallised from heptane at −20° C., giving 6,8-difluoro-3-[2-(6-fluoro-3-pentylchroman-7-yl)vinyl]-2H-chromene as yellow crystals.

Workup

  1. waitthe batch is left
  2. extractionextracted three times with MTB ether
  3. washphases are washed with sat. sodium chloride soln
  4. dry with materialand dried over sodium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe residue is chromatographed on silica gel with heptane/toluene (1:1)
  7. customrecrystallised from heptane at −20° C.

Sources & evidence

ORD record
ord-835e83a830ad48309361a5742bd79618
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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