Lithium borohydride → (7-Aminochroman-2-yl)methanol

HRID 49460Notes

Reaction equation

HRID 49460 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12](OCC)=[O:13])[O:9]2)=[CH:4][CH:3]=1.[BH4-].[Li+]>C1COCC1>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:12][OH:13])[O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 10632774Ethyl 7-Amino-2-chromancarboxylate

Product 1

HCID 10511549(7-Aminochroman-2-yl)methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 7-amino-2-chromancarboxylate (1.26 g, 5.7 mmol) in anhydrous THF is treated dropwise with lithium borohydride (2.0 M in THF, 13.7 mmol), stirred under nitrogen at ambient temperatures for 4 h, quenched with methanol, stirred at ambient temperatures for 1 h, poured into water, extracted with ethyl acetate. The extracts are combined, dried over MgSO4 and concentrated in vacuo to afford the title compound as a nearly colorless oil, 0.9 g (90% yield), identified by NMR and mass spectral analyses.

Workup

  1. customquenched with methanol
  2. stirringstirred at ambient temperatures for 1 h
  3. additionpoured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4622e9e85028411b9225350d39a7c313
Source dataset
uspto-grants-2004_03
Patent number
US06706757B2

Reaction notes

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