2-(N-benzyl-N-methylaminomethyl)chroman-4-one → HCID 20560242, compound

HRID 1659317Notes

Reaction equation

HRID 1659317 reaction equation
[CH2:1]([N:8]([CH2:10][CH:11]1[CH2:20][C:19](=[O:21])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([Li])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCC)C>[CH2:1]([N:8]([CH2:10][CH:11]1[CH2:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([OH:21])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:12]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 205602452-(N-benzyl-N-methylaminomethyl)chroman-4-oneHCID 178506676HCID 178506676, compound

Product 1

HCID 20560242HCID 20560242, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 2-(N-benzyl-N-methylaminomethyl)chroman-4-one (4.9 g) in dry diethyl ether (200 ml) under an atmosphere of dry nitrogen at room temperature, was added a two molar excess of phenyllithium solution and the resulting mixture was boiled for 2 hours before being poured onto ice/dilute HCl. The solution was basified and extracted with ether to give the crude 2-(N-benzyl-N-methylaminomethyl)-4-phenyl-4-hydroxychroman as an orange oil.

Workup

  1. additionbefore being poured onto ice/dilute HCl
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-a633b4e6ce86455885029fc361a3795a
Source dataset
uspto-grants-1981_12
Patent number
US04303656

Reaction notes

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