Sodium hydride → 7-Methyl-2,3-dihydro-1-benzofuran-3-ol

HRID 2096363Notes

Reaction equation

HRID 2096363 reaction equation
[Cl-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[OH:9][C:10]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13]>C1COCC1>[CH3:18][C:17]1[C:10]2[O:9][CH2:2][CH:12]([OH:13])[C:11]=2[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 197819Trimethyloxosulphonium chlorideHCID 5227773-Methylsalicylaldehyde

Product 1

HCID 130130607-Methyl-2,3-dihydro-1-benzofuran-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere 0.945 g (7.35 mmol) trimethylsulphoxonium chloride were placed in 20 mL THF and combined batchwise with 0.300 g (7.50 mmol) sodium hydride (55%, suspension in mineral oil). The reaction mixture was refluxed for 2 h. Then 1.00 g (7.35 mmol) 2-hydroxy-3-methylbenzaldehyde in 20 ml. THF were added dropwise to the reaction mixture and refluxed overnight. Then PE was added and the suspension obtained was filtered. The filtrate was evaporated down i.vac. and purified by flash chromatography. The fractions containing the product were combined and evaporated down.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperaturerefluxed overnight
  3. additionThen PE was added
  4. customthe suspension obtained
  5. filtrationwas filtered
  6. customThe filtrate was evaporated down i.vac
  7. customand purified by flash chromatography
  8. additionThe fractions containing the product
  9. customevaporated down

Sources & evidence

ORD record
ord-a6f2cff8d3d645569089ebcde75f8378
Source dataset
uspto-grants-2013_05
Patent number
US08450327B2

Reaction notes

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