Sodium borohydride → HCID 53710797, compound

HRID 726768Notes

Reaction equation

HRID 726768 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[C:17]2[CH:16]=[C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:14]=[CH:13][C:12]=2[O:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2>C(O)C>[OH:3][CH:4]1[C:17]2[CH:16]=[C:15]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:14]=[CH:13][C:12]=2[O:11][C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12274127Ethyl 9-oxo-9H-xanthene-2-acetate

Product 1

HCID 53710797HCID 53710797, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

5.67 g (150 mmol) of sodium borohydride are added in portions to a solution of 14.2 g (50 mmol) of ethyl 9-oxo-9H-xanthene-2-acetate (Example 10d) in 130 ml of ethanol. The suspension is stirred at room temperature for 15 hours, subsequently diluted with 80 ml of ethanol and poured onto water. The product is extracted with ethyl acetate. The organic phases are washed with an aqueous saturated sodium chloride solution, combined, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. The solid residue is suspended in ethanol, the suspension is filtered and the product is dried under a high vacuum. 6.1 g (43%) of ethyl 9-hydroxy-9H-xanthene-2-acetate, melting point 214°-219° C., results as a white powder.

Workup

  1. additionpoured onto water
  2. extractionThe product is extracted with ethyl acetate
  3. washThe organic phases are washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated on a vacuum rotary evaporator
  6. filtrationthe suspension is filtered
  7. customthe product is dried under a high vacuum

Sources & evidence

ORD record
ord-72622770fa4d45d7b61be2d530a9a644
Source dataset
uspto-grants-1998_01
Patent number
US05710198

Reaction notes

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