Hydrochloric Acid → HCID 59354803, compound

HRID 1776260Notes

Reaction equation

HRID 1776260 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20](OCC)=[O:21])=[CH:15][CH:14]=1.[OH:25]C(C)(C)C(OC)=O.[CH3:33][C:34]([O-:37])([CH3:36])[CH3:35].[K+].Cl>C1COCC1.O>[OH:25][C:33]1[C:34]([CH3:36])([CH3:35])[O:37][C:20](=[O:21])[C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 75024Methyl alpha-hydroxyisobutyrateHCID 23665647Potassium tert-butoxideHCID 58368005Ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

Product 1

HCID 59354803HCID 59354803, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (2.0 g, 0.006 mol) in THF (10 mL), were added methyl 2-hydroxy-2-methylpropaanoate (1.4 g, 0.012 mol) and t-BuOK (1 N, 50 mL) at RT under an inert atmosphere. The mixture was then stirred for 16 h at RT. The reaction mixture was diluted with water, acidified with HCl (1N), and extracted with EtOAc (2×200 mL). The combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo to afford 4-hydroxy-5,5-dimethyl-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (1.0 g, 45%) as a yellow solid.

Workup

  1. extractionextracted with EtOAc (2×200 mL)
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-844b5f5c0f24429bbf04cee8a98c9977
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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