Sodium borohydride → HCID 15458154, compound

HRID 1584749Notes

Reaction equation

HRID 1584749 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:20]=[C:19]3[C:14]([C:15](=[O:21])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+]>CCO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([OH:21])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 15458148HCID 15458148, compound

Product 1

HCID 15458154HCID 15458154, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crude 7-(4'-nitrophenyloxy)-4-chromanone (1.9 g) in EtOH (150 mL) was reduced with NaBH4 (250 mg) at room temperature overnight. The crude product was purified through a column of silica gel (EtOAc:CH2Cl2, 2:8) to give pure 7-(4'-nitrophenyloxy)-4-chromanol (550 mg). This compound (550 mg) was converted to the chloride with thionyl chloride (0.28 g) in CH2Cl2 (30 mL) at 0° C. for 1 hour and then at room temperature for 3 hours. Work-up yielded crude 4-chloro-7-(4'-nitrophenyloxy)-chroman (500 mg). This was heated with N-cyclohexylpiperazine (0.9 g) at 130° C. for one hour. The mixture was then diluted with water (35 mL), made basic with K2CO3 and extracted with EtOAc. The residue from evaporation of the dried organic layer was purified through a column of TLC-grade silica gel (35 g). The desired product was recrystallized rom acetonitrile, m.p. 67-68° C.

Workup

  1. customThe crude product was purified through a column of silica gel (EtOAc:CH2Cl2, 2:8)

Sources & evidence

ORD record
ord-ce1138141b7543a4bba4399ac7443568
Source dataset
uspto-grants-1999_08
Patent number
US05935958

Reaction notes

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