Hydrochloric Acid → HCID 72483451, compound

HRID 2220567Notes

Reaction equation

HRID 2220567 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:30]([O:32][C:33]1[CH:46]=[CH:45][C:36]2[CH:37]3[CH2:43][CH2:42][C:41](=O)[CH2:40][CH:38]3[O:39][C:35]=2[C:34]=1[F:47])[CH3:31].Cl>C1COCC1.O>[CH2:30]([O:32][C:33]1[CH:46]=[CH:45][C:36]2[CH:37]3[CH2:43][CH2:42][C:41](=[CH:2][O:3][CH3:4])[CH2:40][CH:38]3[O:39][C:35]=2[C:34]=1[F:47])[CH3:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 68447935HCID 68447935, compound

Product 1

HCID 72483451HCID 72483451, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

58.3 g (170 mmol) of methoxymethyltriphenylphosphonium chloride are initially introduced in 500 ml of THF, and a solution of 19.1 g (170 mmol) of potassium tert-butoxide in 200 ml of THF is added at 0° C. After 30 min at this temperature, 7-ethoxy-6-fluoro-1,4,4a,9b-tetrahydro-2H-dibenzofuran-3-one as a solution in 300 ml of THF is added, and the batch is stirred at room temperature for 17 h. Water is added at 0° C., and the mixture is acidified using 2 N hydrochloric acid. The batch is extracted with MTBE, and the combined extracts are washed with sat. sodium chloride solution. The solution is dried using sodium sulfate and concentrated to dryness. Purification of the crude product by column chromatography (SiO2, toluene) gives (±)-(4aR*, 9bS*)-7-ethoxy-6-fluoro-3-[1-methoxy-methylidene]-1,2,3,4,4a,9b-hexahydrodibenzofuran as colourless solid.

Workup

  1. extractionThe batch is extracted with MTBE
  2. washthe combined extracts are washed with sat. sodium chloride solution
  3. customThe solution is dried
  4. concentrationconcentrated to dryness
  5. customPurification of the crude product by column chromatography (SiO2, toluene)

Sources & evidence

ORD record
ord-a5946ac27f354ad88897dd4441c93717
Source dataset
uspto-grants-2008_08
Patent number
US07417157B2

Reaction notes

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