Acetic Acid → 2-(N-benzyl-N-methylaminomethyl)chroman-4-one

HRID 1659316Notes

Reaction equation

HRID 1659316 reaction equation
[CH2:1]([N:8]([CH2:10][C:11]1[O:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)(=O)C>O1CCCC1>[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

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 20560229HCID 20560229, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 205602452-(N-benzyl-N-methylaminomethyl)chroman-4-oneYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A stirred solution of 2-(N-benzyl-N-methylaminomethyl)chromone (15.6 g) in dry tetrahydrofuran (400 ml) at -78° C., was treated with a suspension of LiAlH4 (3.2 g) in dry tetrahydrofuran (50 ml) and the resulting mixture was stirred at -78° C. for 4 hours before being acidified with glacial acetic acid and allowed to stand at room temperature for 17 hours. The mixture was then filtered and the filtrate was evaporated, dissolved in chloroform and washed with water. The dried, evaporated organic extracts gave an oil which was chromatographed on alumina eluting with ether to give the title compound as a yellow oil (4.9 g).

Workup

  1. waitto stand at room temperature for 17 hours
  2. filtrationThe mixture was then filtered
  3. customthe filtrate was evaporated
  4. dissolutiondissolved in chloroform
  5. washwashed with water
  6. customThe dried, evaporated organic extracts
  7. customgave an oil which
  8. customwas chromatographed on alumina eluting with ether

Sources & evidence

ORD record
ord-6fa76710081e42ac9ea7bba502001f95
Source dataset
uspto-grants-1981_12
Patent number
US04303656

Reaction notes

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