Water → HCID 29938143, compound

HRID 324606Notes

Reaction equation

HRID 324606 reaction equation
[H-].[Na+].[O:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.[O:8]1[C:12]2[CH:13]=[CH:14][C:15]([CH:17]=O)=[CH:16][C:11]=2[CH2:10][CH2:9]1.[OH2:19]>>[O:3]1[C:7]2[CH:13]=[CH:14][C:15](/[CH:16]=[CH:11]/[C:12]([O:8][CH2:9][CH3:10])=[O:19])=[CH:17][C:6]=2[CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 7359012,3-Dihydrobenzofuran-5-carboxaldehyde

Product 1

HCID 29938143HCID 29938143, compoundYield 88%

Procedure

60% sodium hydride (3.39 g, 84.6 mmols) was added to a tetrahydrofuran (150 ml) solution of triethyl phosphonoacetate (19.0 g, 84.6 mmols) while cooling with ice, and the mixture was stirred for 20 minutes. To this was dropwise added a tetrahydrofuran (15 ml) solution of 2,3-dihydrobenzofuran-5-carbaldehyde (11.4 g, 76.9 mmols) and stirred further for 1 hour. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was washed with a saturated saline solution, then dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica-gel column chromatography (hexane/ethyl acetate=from 95/5 to 9/1) to obtain 14.7 g (yield: 88%) of the target compound. This was oily.

Workup

  1. temperaturewhile cooling with ice
  2. stirringstirred further for 1 hour
  3. extractionwas then extracted with ethyl acetate
  4. washThe extract was washed with a saturated saline solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified through silica-gel column chromatography (hexane/ethyl acetate=from 95/5 to 9/1)

Sources & evidence

ORD record
ord-1a301f0581094c789ed1e453a277d594
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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