8-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-3H-benzo[f]chromene → 8-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-2,3-dihydro-1H-benzo[f]chromene

HRID 1873326Notes

Reaction equation

HRID 1873326 reaction equation
[CH2:1]([O:3][C:4]1[CH:28]=[CH:27][C:7]2[C:8]3[CH:9]=[CH:10][CH:11]([CH:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19]4)[O:12][C:13]=3[C:14]([F:17])=[C:15]([F:16])[C:6]=2[CH:5]=1)[CH3:2]>C1COCC1.[Pd]>[CH2:1]([O:3][C:4]1[CH:28]=[CH:27][C:7]2[C:8]3[CH2:9][CH2:10][CH:11]([CH:18]4[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19]4)[O:12][C:13]=3[C:14]([F:17])=[C:15]([F:16])[C:6]=2[CH:5]=1)[CH3:2]

Participants

4

Reactant 1

HCID 581518988-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-3H-benzo[f]chromene

Product 1

HCID 581519288-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-2,3-dihydro-1H-benzo[f]chromene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5.1 g (13.1 mmol) of 8-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-3H-benzo[f]chromene are hydrogenated at atmospheric pressure in THF and in the presence of Pd/C (5% of Pd). The reaction solution is filtered, and the filtrate is evaporated to dryness. The residue is recrystallised from ethyl acetate, giving 8-ethoxy-5,6-difluoro-3-(4-propylcyclohexyl)-2,3-dihydro-1H-benzo[f]chromene as a colourless solid (m.p. 158° C.).

Workup

  1. filtrationThe reaction solution is filtered
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-7fed7daebff44f0f89356262ba76d98b
Source dataset
uspto-grants-2012_11
Patent number
US08303844B2

Reaction notes

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