Ethyl 7-(Formylamino)chroman-2-carboxylate → [7-(Methylamino)-3,4-dihydro-2H-chromen-2-yl]methanol

HRID 49465

Reaction equation

HRID 49465 reaction equation
[CH:1]([NH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([C:14](OCC)=[O:15])[O:11]2)=[CH:6][CH:5]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][NH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH:10]([CH2:14][OH:15])[O:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 20637412Ethyl 7-(Formylamino)chroman-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11480975[7-(Methylamino)-3,4-dihydro-2H-chromen-2-yl]methanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 7-(formylamino)chroman-2-carboxylate (1.54 g; 6.00 mmol) in anhydrous THF, under nitrogen, is treated dropwise with a 1 M solution of lithium aluminum hydride in THF (30 mL; 30 mmol), stirred at ambient temperature for 4 h, quenched with a 10% solution of water in THF, with cooling as necessary to maintain room temperature, poured into water and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound as a straw colored oil (1.13 g; 98% yield), identified by NMR spectral analysis.

Workup

  1. customquenched with a 10% solution of water in THF
  2. temperaturewith cooling as necessary
  3. temperatureto maintain room temperature
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washThe combined extracts are washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2edac40d02fd4847a204010bb8f8c0c6
Source dataset
uspto-grants-2004_03
Patent number
US06706757B2

Linked notes

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