Formic Acid → HCID 58212295, compound

HRID 1095250Notes

Reaction equation

HRID 1095250 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH:22]4[CH2:31][CH2:30][C:25]5(OCC[O:26]5)[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[C:12]([F:32])[CH:11]=2)[CH2:6][CH2:5]1)[CH3:2].C(O)=O.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][CH:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]3[CH2:21][CH2:20][CH:19]([CH:22]4[CH2:31][CH2:30][C:25](=[O:26])[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[C:12]([F:32])[CH:11]=2)[CH2:8][CH2:9]1)[CH3:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 66781621HCID 66781621, compound

Product 1

HCID 58212295HCID 58212295, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

The compound (25) (31.4 g), formic acid (90 g) and toluene (90 ml) were put in a reaction vessel under a nitrogen atmosphere, heated under reflux for 3 hours, and cooled slowly to room temperature. Water (200 ml) and toluene (200 ml) were added and mixed thereto. The mixture was allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=9:1 by volume) as an eluent and silica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of toluene and heptane (toluene: heptane=1:1 by volume), and dried, giving 7.51 g of 4′-(4-(4-ethoxycyclohexyl)-2-fluorophenyl)bi(cyclohexane)-4-one (26). The yield based on the compound (25) was 26.6%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. additionmixed
  4. customhad separated into two phases
  5. washwashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated under reduced pressure
  8. customthe residue was purified with a fractional operation by means of column chromatography
  9. customsilica gel as a stationary phase powder, and further purified by means of recrystallization from a mixed solvent of toluene and heptane (toluene: heptane=1:1 by volume)
  10. customdried

Sources & evidence

ORD record
ord-110d0733bdbf42da9822ceeb976cff9c
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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