Reaction #2254171

ord-2495ae740b9140b7a78e5059f475cd15

Reaction equation

[BH4-].[Na+]
sodium borohydride
CCO
ethanol
CCOC(=O)c1cc(=O)c2ccc(O)cc2o1
Ethyl 7-hydroxychromen-4-one-2-carboxylate
[Ca+2].[Cl-].[Cl-]
calcium chloride
[BH4-].[Na+]
Sodium borohydride
COc1cc(=O)c2ccc(O)cc2o1
2-methoxy-7-hydroxy-4H-chromen-4-one

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureagain cooled
  2. 2
    workup.STIRRINGThe mixture is stirred overnight at RT

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09044409B2uspto-grants-2015_06