Potassium Carbonate → HCID 90404905, compound

HRID 2277038Notes

Reaction equation

HRID 2277038 reaction equation
[C:1]([O-:4])([O-])=O.[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([O:13][CH3:14])=[O:12]>CN(C=O)C>[O:4]1[CH2:1][CH2:11][CH:10]([CH2:15][O:7][C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 90404905HCID 90404905, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

K2CO3 (8.2 g, 59.2 mmol) was added to a stirred solution of methyl 3-hydroxybenzoate (11) (3.0 g, 19.72 mmol) sulfonate (10) (5.33 g, 19.72 mmol) in DMF (30 mL) and the reaction mixture was stirred at 90° C. for 16 h. The reaction mixture was concentrated under reduced pressure. Purification by column chromatography (100-200 silica mesh, 30% EtOAc in hexanes) gave methyl 3-((tetrahydro-2H-pyran-4-yl)methoxy)benzoate (12) as a light yellow solid. Yield (4.8 g, 97%); 1H NMR (400 MHz, DMSO-d6) δ 7.53 (d, J=7.6 Hz, 1H), 7.44-7.40 (m, 2H), 7.22 (dd, J=8.4, 2.4 Hz, 1H), 3.88-3.82 (m, 7H), 3.32 (t, J=1.2 Hz, 2H), 2.02-1.96 (m, 1H), 1.69-1.66 (m, 2H), 1.38-1.28 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customPurification by column chromatography (100-200 silica mesh, 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-67a8629053f34a7eb8e40929f367d4e6
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

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