m-Anisoyl chloride → HCID 67385413, compound

HRID 912107Notes

Reaction equation

HRID 912107 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].C[Si](C)(C)[N-][Si](C)(C)C.[Li+].O.[C:23](=[O:26])(O)[O-:24].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([CH:10]1[CH2:11][CH:3]=[CH:4][O:24][C:23]1=[O:26])=[O:7]

Participants

5

Reactant 3

HCID 74374m-Anisoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 86585896Sodium bicarbonate water

Product 1

HCID 67385413HCID 67385413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-valerolactone (2.0 g, 20 mmol) in anhydrous tetrahydrofuran (100 ml) was cooled to −78° C. under a nitrogen atmosphere, and 3-methoxybenzoyl chloride (3.58 g, 21 mmol) and lithium hexamethyldisilazide (40 ml, 1M tetrahydrofuran solution, 40 mmol) were added sequentially. Stirring was carried out for 2 hours, followed by treatment with saturated sodium bicarbonate water. The reaction mixture was extracted with ethyl acetate (100 ml), followed by washing with brine, and subsequently, the solvent was distilled off under reduced pressure, to obtain a brown crude product. Purification by silica gel column chromatography (hexane/ethyl acetate=1/1) afforded the desired compound as a pale yellow liquid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (100 ml)
  2. washby washing with brine
  3. distillationsubsequently, the solvent was distilled off under reduced pressure
  4. customto obtain a brown crude product
  5. customPurification by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4269f162246d402e977ccc5185b88886
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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