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

HRID 469364

Reaction equation

HRID 469364 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 0.300 g (7.50 mmol) sodium hydride (55%, suspension in mineral oil) were added batchwise. 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 it was 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. temperaturewas refluxed overnight
  3. additionThen PE was added
  4. customthe suspension obtained
  5. filtrationwas filtered
  6. customThe filtrate was evaporated down i
  7. customand purified by flash chromatography
  8. additionThe fractions containing the product
  9. customevaporated down

Sources & evidence

ORD record
ord-83e49fa21a4c4926ac8c167607bd148d
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Linked notes

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