Hydrochloric Acid → HCID 46195897, compound

HRID 2360100Notes

Reaction equation

HRID 2360100 reaction equation
[OH:1][C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3O)=[CH:8][O:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].O.Cl>C(O)C>[CH3:12][C:11]1[C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[C:10]=1[O:9][CH2:8][CH:7]1[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:20][CH:6]21

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 58030373HCID 58030373, compound

Product 1

HCID 46195897HCID 46195897, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 7-hydroxy-3-(2-hydroxy-phenyl)-8-methyl-chromen-4-one (3 gm, 11.2 mmol) in absolute ethanol (30 ml) at 0° C. was added NaBH4 (2.6 gm, 67.2 mmol). The reaction mixture was then stirred for 24 hours at room temperature. The reaction was stopped by adding ice-cooled water and the solution was neutralized with 10% HCl to get the white precipitate. The white precipitate was washed with water and the purified by silica gel column chromatography using hexane-chloroform as the eluent to give 4-methyl-6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromen-3-ol (1.56 gm, 55%) as white solid.

Workup

  1. additionby adding ice-
  2. customto get the white precipitate
  3. washThe white precipitate was washed with water
  4. customthe purified by silica gel column chromatography

Sources & evidence

ORD record
ord-723ae78460de4257aa13dd63687f16a0
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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