Hydrochloric Acid → HCID 70849514, compound

HRID 2220565Notes

Reaction equation

HRID 2220565 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:21][CH2:20][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:14][CH:13]2[OH:22])=[C:8](F)[C:7]=1[F:24])[CH3:4].O.Cl>CCCCC.C1(C)C=CC=CC=1.CN(C=O)C>[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]2[CH:12]3[CH2:21][CH2:20][C:15]4([O:19][CH2:18][CH2:17][O:16]4)[CH2:14][CH:13]3[O:22][C:8]=2[C:7]=1[F:24])[CH3:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 58991866HCID 58991866, compound

Product 1

HCID 70849514HCID 70849514, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8003PentaneSolvent

Conditions

Temperature
90 °C

Procedure

50.0 g (1.25 mol) of sodium hydride (60% suspension in mineral oil) are washed repeatedly with n-pentane and suspended in 3000 ml of toluene. The suspension is heated to 90° C., and a solution of 145.0 g (0.46 mol) of 8-(4-ethoxy-2,3-difluorophenyl)-1,4-dioxaspiro[4.5]decan-7-ol in 700 ml of DMF is slowly metered in. The batch is stirred at 90° C. for 30 h, cooled and hydrolysed using water. The mixture is neutralised by addition of 2 N hydrochloric acid, and the organic phase is separated off. The aqueous phase is extracted with toluene, and the combined organic phases are washed with sat. sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness under reduced pressure. The crude product obtained is recrystallised from ethanol at 5° C., giving (±)-(4aR*, 9bS*)-7-ethoxy-6-fluoro-1,4,4a,9b-tetrahydro-2H-spiro-[dibenzo[b,d]-furan-3,2′-1,3-dioxolane] as colourless solid.

Workup

  1. temperaturecooled
  2. customthe organic phase is separated off
  3. extractionThe aqueous phase is extracted with toluene
  4. washthe combined organic phases are washed with sat. sodium chloride solution
  5. customThe solution is dried
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe crude product obtained
  8. customis recrystallised from ethanol at 5° C.

Sources & evidence

ORD record
ord-110bbf33604e44d1b11aed490f0749f1
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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