Benzoic acid, 3-formyl-4-hydroxy-, methyl ester → HCID 53256703, compound

HRID 404362Notes

Reaction equation

HRID 404362 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])=[O:2].[CH:14]1([Mg]Br)[CH2:16][CH2:15]1>C1COCC1>[CH:14]1([CH:1]([OH:2])[C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=2[OH:13])[C:6]([O:8][CH3:9])=[O:7])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 212595Benzoic acid, 3-formyl-4-hydroxy-, methyl esterHCID 178418630HCID 178418630, compound

Product 1

HCID 53256703HCID 53256703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In an ice-bath, methyl 3-formyl-4-hydroxybenzoate T29.1 (900 mg, 5 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) was dissolved in 5 mL THF. Then cyclopropylmagnesium bromide, 0.5 m in THF (22000 μL, 11 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) was added slowly. The reaction was raised to room temperature immediately and stirred at room temperature for 2 hours. After quenching with 1N HCl 11 mL, the reaction was extracted with EtOAc and dried. Silica gel chromatography afforded 950 mg of the product T29.2 (85%).

Workup

  1. addition, USA) was added slowly
  2. customAfter quenching with 1N HCl 11 mL
  3. extractionthe reaction was extracted with EtOAc
  4. customdried

Sources & evidence

ORD record
ord-2c111e659d4f4526965e2b84da616715
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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