Hydrochloric Acid → HCID 86615831, compound

HRID 2220574Notes

Reaction equation

HRID 2220574 reaction equation
[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]=[CH:16][CH3:17])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:20])[CH3:2].[Na+].C1(S([O-])=O)C=CC=CC=1.Cl.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]=[CH:16]/[CH3:17])[CH2:11][CH:9]3[O:10][C:6]=2[C:5]=1[F:20])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723840Benzenesulfinic acid, sodium saltHCID 72483448HCID 72483448, compound

Product 1

HCID 86615831HCID 86615831, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6.0 g (about 21.7 mmol) of (E/Z) isomer mixture of (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-3-propenyl-1,2,3,4,4a,9b-hexahydrodibenzofuran (see 1.9) are refluxed in 60 ml of toluene together with 1.15 g (7.0 mmol) of benzene-sulfinic acid sodium salt and 21.4 ml of 1 N hydrochloric acid. After 1 h, the mixture is added to water, and the organic phase is separated off. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with sat. sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. Repeated recrystallisation from isopropanol gives (±)-(3R*, 4aR*, 9bS*)-7-ethoxy-6-fluoro-3-((E)-propenyl)-1,2,3,4,4a,9b-hexahydrodibenzofuran as colourless solid (melting point 145° C.).

Workup

  1. customthe organic phase is separated off
  2. extractionThe aqueous phase is extracted with MTBE
  3. washthe combined organic phases are washed with sat. sodium chloride solution
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customrecrystallisation from isopropanol

Sources & evidence

ORD record
ord-76ebfbdb229045d3a0e8c24cce6d8add
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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