Sodium borohydride → HCID 53710797, compound
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]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.