Sodium hydride → HCID 22725339, compound

HRID 1876424Notes

Reaction equation

HRID 1876424 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:15])([CH3:14])[CH2:12]Cl)[CH:5]=1>O1CCCC1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:12][C:11]([CH3:15])([CH3:14])[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 58566715HCID 58566715, compound

Product 1

HCID 22725339HCID 22725339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (1.44 g, 36 mmol) in anhydrous tetrahydrofuran was added 4-chloro-2-(1-chloro-2-methylpropan-2-yl)phenol (721) (6.6 g, 30.0 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour. The reaction was quenched with methanol, diluted with water, and extracted with ether. The ethereal extract was washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified by flash chromatography on silica gel to give 5-chloro-3,3-dimethyl-2,3-dihydrobenzofuran (722).

Workup

  1. customThe reaction was quenched with methanol
  2. additiondiluted with water
  3. extractionextracted with ether
  4. extractionThe ethereal extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-85afc3536f744fa4b96668c2330cb0f7
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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