Acetic Acid → HCID 13883265, compound

HRID 1608266Notes

Reaction equation

HRID 1608266 reaction equation
[CH:1]([Mg]Cl)=[CH2:2].[CH:5]([C:7]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH:8]=1)=[O:6].[Cl-].[NH4+].C(O)(=O)C>O1CCCC1>[OH:6][CH:5]([C:7]1[CH:11]=[C:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH:8]=1)[CH:1]=[CH2:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 25517Ammonium ChlorideHCID 13883264HCID 13883264, compoundHCID 178461836HCID 178461836, compound

Product 1

HCID 13883265HCID 13883265, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

46.5 ml of a 1.5M solution of vinylmagnesium chloride in tetrahydrofuran are initially taken in 60 ml of absolute tetrahydrofuran at 0° C. 11.9 g of 3-formyl-5-(p-fluorobenzyl)-furan in 60 ml of absolute tetrahydrofuran are added dropwise at 0°-10° C. to the stirred mixture in the absence of moisture, and stirring is continued for 15 hours at room temperature. 100 ml of a saturated ammonium chloride solution and 20 ml of glacial acetic acid are added carefully to the reaction mixture, the precipitate dissolving. The mixture is extracted three times by shaking with ether, after which the combined ether extracts are washed with water, dried over sodium sulfate and evaporated down under reduced pressure. The oil obtained (14 g) is purified by column chromatography over silica gel using toluene/acetone (9/1) as the eluent. 7.1 g of 3-(1-hydroxy-2-propenyl)-5-(p-fluorobenzyl)-furan are obtained as an oil (nD22 : 1.5370). ##STR15##

Workup

  1. dissolutionthe precipitate dissolving
  2. extractionThe mixture is extracted three times
  3. stirringby shaking with ether
  4. washafter which the combined ether extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated down under reduced pressure
  7. customThe oil obtained (14 g)
  8. customis purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-29a22892aea84aea82caba89c554d037
Source dataset
uspto-grants-1989_09
Patent number
US04870100

Reaction notes

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