Ethanol → 7-Hydroxy-2-methoxy-4H-1-benzopyran-4-one

HRID 2166989Notes

Reaction equation

HRID 2166989 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[CH:7]=[C:8](C(OCC)=O)[O:9]2)=[CH:4][CH:3]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].[CH2:23]([OH:25])C>>[CH3:23][O:25][C:8]1[O:9][C:10]2[C:5]([C:6](=[O:17])[CH:7]=1)=[CH:4][CH:3]=[C:2]([OH:1])[CH:11]=2

Participants

5

Reactant 4

HCID 702EthanolHCID 4311764Sodium borohydride2×HCID 5284359Calcium ChlorideHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Product 1

HCID 231051467-Hydroxy-2-methoxy-4H-1-benzopyran-4-one

Procedure

Ethyl 7-hydroxychromen-4-one-2-carboxylate (2 g, 8.538 mmol) and granulated and dried calcium chloride (1 g, 9.01 mmol) are initially introduced, and ethanol (absolute, 40 ml) is added. Sodium borohydride (1.33 g, 35.157 mmol) is subsequently added in portions with ice cooling. The reaction mixture is stirred at RT for 2 hours, then again cooled using an ice bath, and sodium borohydride (0.45 g, 11.895 mmol) is again added. The mixture is stirred overnight at RT.

Workup

  1. temperatureagain cooled
  2. stirringThe mixture is stirred overnight at RT

Sources & evidence

ORD record
ord-2495ae740b9140b7a78e5059f475cd15
Source dataset
uspto-grants-2015_06
Patent number
US09044409B2

Reaction notes

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