Methanol → 2-(4-Chlorophenyl)tetrahydro-2-furancarboxylic acid

HRID 2229484Notes

Reaction equation

HRID 2229484 reaction equation
[C-]#N.[K+].Cl[CH2:5][CH2:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)=[O:9].[OH2:17].[CH3:18][OH:19]>>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2([C:18]([OH:19])=[O:17])[CH2:7][CH2:6][CH2:5][O:9]2)=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 9032Potassium CyanideHCID 27237814,4'-Dichlorobutyrophenone

Product 1

HCID 184678832-(4-Chlorophenyl)tetrahydro-2-furancarboxylic acid

Procedure

Potassium cyanide (1.87 g, 28.78 mmol) was added to a solution of 4-chloro-4′-chloro-butyrophenone (5.00 g, 23.03 mmol) in 25 mL of methanol. After stirring for 3 days at room temperature, the reaction was poured into water (50 mL) and extracted with methylene chloride (3×50 mL). The organic layers were combined, washed with saturated aqueous sodium chloride (50 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (Biotage) over silica gel eluting with hexane/ethyl acetate (30:1) to give 3.52 g of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ 7.47 (m, 2H); 7.38 (m, 2H); 4.24 (m, 2H); 2.74 (m, 1H); 2.33 (m, 1H), 2.15 (m, 2H).

Workup

  1. extractionextracted with methylene chloride (3×50 mL)
  2. washwashed with saturated aqueous sodium chloride (50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (Biotage) over silica gel eluting with hexane/ethyl acetate (30:1)

Sources & evidence

ORD record
ord-3b26ffa5124247f5a2f2a65c1cca4403
Source dataset
uspto-grants-2002_07
Patent number
US06420418B1

Reaction notes

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