Sodium hydride → 4-(3-chloro-4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one

HRID 446820Notes

Reaction equation

HRID 446820 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]([O:22][CH2:23][C:24]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([Cl:34])[CH:27]=2)=O)=[O:21])=[CH:15][CH:14]=1.[H-].[Na+]>CN(C=O)C>[Cl:34][C:28]1[CH:27]=[C:26]([C:24]2[CH2:23][O:22][C:20](=[O:21])[C:19]=2[C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:1]=3)=[CH:18][CH:17]=2)[CH:31]=[CH:30][C:29]=1[O:32][CH3:33]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 583680212-(3-Chloro-4-methoxyphenyl)-2-oxoethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate

Product 1

HCID 583680064-(3-chloro-4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-oneYield 6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of 2-(3-chloro-4-methoxyphenyl)-2-oxo-ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (750 mg, 1.58 mmol) in DMF (10 mL) was added NaH (190 mg, 3.95 mmol). The reaction mixture was then stirred at RT for 1 h, quenched with ice and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-(3-chloro-4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (40 mg, 6%) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 8.42-8.38 (m, 1H), 8.16-8.05 (m, 2H), 7.72 (t, J=7.6 Hz, 1H), 7.49-7.39 (m, 2H), 7.66 (d, J=8.2 Hz, 1H), 7.58 (t, J=7.2 Hz, 1H), 7.42-7.36 (m, 1H), 7.29-7.20 (m, 2H), 7.17-7.10 (m, 2H), 5.45 (s, 2H), 5.23 (s, 2H), 3.85 (s, 3H). MS: M+H: m/z=458.1. HPLC: 93%, (Condition-H).

Workup

  1. customquenched with ice
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto obtain the crude product
  7. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-2cf8d309662546eb9f441b433c0ae611
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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