Formic Acid → HCID 72483450, compound

HRID 2220568Notes

Reaction equation

HRID 2220568 reaction equation
[CH2:1]([O:3][C:4]1[CH:19]=[CH:18][C:7]2[CH:8]3[CH2:14][CH2:13][C:12](=[CH:15][O:16]C)[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:20])[CH3:2].C(O)=O.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:19]=[CH:18][C:7]2[CH:8]3[CH2:14][CH2:13][CH:12]([CH:15]=[O:16])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:20])[CH3:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 72483451HCID 72483451, compound

Product 1

HCID 72483450HCID 72483450, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.0 g (28.7 mmol) of (±)-(4aR*, 9bS*)-7-ethoxy-6-fluoro-3-[1-methoxy-methylidene]-1,2,3,4,4a,9b-hexahydrodibenzofuran are dissolved in 200 ml of toluene and stirred vigorously at room temperature for 18 h together with 30 ml (0.80 mol) of formic acid and 0.5 ml (27.8 mmol) of water. The organic phase is separated off and washed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. Purification by column chromatography (SiO2, toluene:ethyl acetate=99:1) gives a mixture (64:36) of (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-carbaldehyde and (±)-(3S*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-carbaldehyde.

Workup

  1. customThe organic phase is separated off
  2. washwashed successively with water, sat. sodium hydrogencarbonate solution and sat. sodium chloride solution
  3. customThe solution is dried
  4. concentrationconcentrated to dryness
  5. customPurification by column chromatography (SiO2, toluene:ethyl acetate=99:1)

Sources & evidence

ORD record
ord-1c01ef6f88af448a9babd86be9f586f5
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

Loading…