Tetrahydrofuran → HCID 57804168, compound

HRID 2102933Notes

Reaction equation

HRID 2102933 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]2[CH2:16][CH2:15]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].C1COCC1>CO>[Cl:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]2[CH2:16][CH2:15]2)[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57804234HCID 57804234, compound

Product 1

HCID 57804168HCID 57804168, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 2-chloro-4-(2-cyclopropylethynyl)benzoate (310 mg, 0.0013 mol), 2N aq. NaOH (3.0 mL), THF (5 mL), and MeOH (5 mL) was stirred at rt for 5 h. The mixture was concentrated under vacuum and the residue was treated with water and acidified with 1N HCl to pH 2-3, and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated under vacuum to give the product (270 mg, 93%) as a yellow solid. LC-MS: 3.18 min, 218.9 & 220.9 (M−1).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue was treated with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5c1b4e9f8a77464fb076b723ae2ed836
Source dataset
uspto-grants-2009_08
Patent number
US07576099B2

Reaction notes

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