Nitrogen → HCID 86666550, compound

HRID 2098335Notes

Reaction equation

N#N.[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([OH:21])[CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].F[C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][CH:30]=1>O.CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([O:21][C:29]2[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][CH:30]=2)[CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a single necked round bottomed flask (500 mL) fitted with N2(g) balloon, Methyl 3-benzyloxy-5-hydroxybenzoate (Intermediate 5) (24 g, 93 mmol, 1 equiv.) followed by DMF (130 mL, 5 v/w) were added. To this stirring solution, potassium carbonate (38 g, 279 mmol, 3 equiv.) was added at room temperature. The mixture was stirred at the same temperature for 10 minutes. 4-Fluorobenzaldehyde (13.84 g, 111.62 mmol, 1.2 equiv.) was added. The reaction mixture was heated at 90° C. for 16 h. The progress of the reaction was monitored by TLC. After completion, the reaction was diluted with water and extracted with ethyl acetate. Combined organic layers were washed with brine and dried over anhydrous sodium sulphate to furnish title compound as thick yellow liquid (32.5 g). The product can be purified by column chromatography by eluting with 10% ethyl acetate:pet ether as mobile phase.

Workup

additionwere added
extractionextracted with ethyl acetate
washCombined organic layers were washed with brine
dry with materialdried over anhydrous sodium sulphate

Sources & evidence

ORD record: ord-8633b4d69a154434aca96c69eb9cd9e8
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450494B2

Reaction notes

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