Formic Acid → HCID 68447935, compound

HRID 2220566Notes

Reaction equation

HRID 2220566 reaction equation
[CH2:1]([O:3][C:4]1[CH:20]=[CH:19][C:7]2[CH:8]3[CH2:18][CH2:17][C:12]4(OCC[O:13]4)[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:21])[CH3:2].C(O)=O.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:20]=[CH:19][C:7]2[CH:8]3[CH2:18][CH2:17][C:12](=[O:13])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:21])[CH3:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 70849514HCID 70849514, compound

Product 1

HCID 68447935HCID 68447935, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

135.0 g (459 mmol) of (±)-(4aR*, 9bS*)-7-ethoxy-6-fluoro-1,4,4a,9b-tetrahydro-2H-spiro[dibenzo[b,d]furan-3,2′-1,3-dioxolane] are dissolved in 1800 ml of toluene and stirred vigorously together with 550 ml (14.6 mol) of formic acid with addition of 10.0 ml (0.56 mol) of water. After 18 h, the organic phase is separated off, and the formic acid is extracted with toluene. The combined organic phases are washed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution and dried using sodium sulfate. The crude product remaining after removal of the solvent is purified by column chromatography (SiO2, toluene:ethyl acetate=4:1), giving (±)-(4aR*, 9bS*)-7-ethoxy-6-fluoro-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one as colourless solid.

Workup

  1. customthe organic phase is separated off
  2. extractionthe formic acid is extracted with toluene
  3. washThe combined organic phases are washed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution
  4. customdried
  5. customafter removal of the solvent
  6. customis purified by column chromatography (SiO2, toluene:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-fbc7cbffa22842628399d1dee66788ad
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

Loading…