ethyl 3,4-dihydro-1H-2-benzopyran-1-acetate → 2-(3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid

HRID 1774009Notes

Reaction equation

HRID 1774009 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][O:7]1)C>C1COCC1.CO.[OH-].[Na+]>[CH:6]1([CH2:5][C:4]([OH:16])=[O:3])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][O:7]1

Participants

5

Reactant 1

HCID 10822798ethyl 3,4-dihydro-1H-2-benzopyran-1-acetate

Product 1

HCID 133088642-(3,4-dihydro-1H-2-benzopyran-1-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of (±)-isochroman-1-yl-acetic acid ethyl ester (1.90 g, 8.63 mmol, 1 eq.) in THF (40 mL) and MeOH (10 mL), 1M aq. NaOH soln. (17.3 mL, 17.3 mmol, 2 eq.) was added. The pale yellow solution was stirred at r.t. for 2 hours, then the organic solvents were removed in vacuo. The aq. layer was washed with AcOEt (1×10 mL). The aq. layer was acidified with 1N aq. HCl (pH=1). The resulting emulsion was extracted with DCM (3×25 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo to give the title compound as a colorless oil that solidifies upon standing. The product was used without further purification.

Workup

  1. addition(17.3 mL, 17.3 mmol, 2 eq.) was added
  2. customthe organic solvents were removed in vacuo
  3. washThe aq. layer was washed with AcOEt (1×10 mL)
  4. extractionThe resulting emulsion was extracted with DCM (3×25 mL)
  5. dry with materialphases were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee9b7be4bf3b4eada028aadb8b9aa568
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

Loading…