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

HRID 2420651Notes

Reaction equation

HRID 2420651 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[O:8][CH2:7][C:6]([CH:13]=[CH:14][C:15]1[CH:24]=[C:23]3[C:18]([CH2:19][CH:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:21][O:22]3)=[CH:17][C:16]=1[F:30])=[CH:5]2>C1COCC1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[O:8][CH2:7][C:6]([CH2:13][CH2:14][C:15]1[CH:24]=[C:23]3[C:18]([CH2:19][CH:20]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:21][O:22]3)=[CH:17][C:16]=1[F:30])=[CH:5]2

Participants

4

Reactant 1

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

Product 1

HCID 672156416,8-Difluoro-3-[2-(6-fluoro-3-pentylchroman-7-yl)ethyl]-2H-chromene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

6,8-Difluoro-3-[2-(6-fluoro-3-pentylchroman-7-yl)vinyl]-2H-chromene is dissolved in THF and hydrogenated to completion on a palladium/active carbon catalyst. The catalyst is filtered off, the solution is evaporated, the residue is filtered through silica gel with toluene/heptane (3:2), and the crude product is recrystallised from n-heptane at −25° C., giving colourless crystals of m.p. 84° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solution is evaporated
  3. filtrationthe residue is filtered through silica gel with toluene/heptane (3:2)
  4. customthe crude product is recrystallised from n-heptane at −25° C.
  5. customgiving colourless crystals of m.p. 84° C.

Sources & evidence

ORD record
ord-0a742841cf404074ab18670d412b94fc
Source dataset
uspto-grants-2011_06
Patent number
US07955664B2

Reaction notes

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