Ammonium Chloride → 3-(3-Carbomethoxyphenyl)methyl-4,6-dihydroxy-chroman

HRID 1886090Notes

Reaction equation

HRID 1886090 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:11][CH:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:23])[CH:19]=3)[O:14][CH2:13]2)[CH:8]=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2].[BH4-].[Na+].[NH4+].[Cl-]>CO.C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH2:11][CH:12]2[CH:21]([OH:22])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([OH:23])[CH:19]=3)[O:14][CH2:13]2)[CH:8]=[CH:9][CH:10]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 190914643-(3-Carbomethoxyphenyl)methyl-6-hydroxy-4-chromanone

Product 1

HCID 196006813-(3-Carbomethoxyphenyl)methyl-4,6-dihydroxy-chroman

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Step 3 (700 mg, 2.4 mmol) in 5 ml MeOH and 1 ml THF at r.t. was added NaBH4 (80 mg, 2.4 mmol). The solution was stirred at r.t. for 0.5 hr. The mixture was poured into cold NH4Cl solution, extracted with HOAc, and chromatographed on silica gel (eluted with 40% EtOAc/hexane) to give 441 mg (58%) of the cis isomer and 279 mg (37%) of the trans isomer of the title compound.

Workup

  1. extractionextracted with HOAc
  2. customchromatographed on silica gel (eluted with 40% EtOAc/hexane)

Sources & evidence

ORD record
ord-9eb89e20c928472284e7909d12989173
Source dataset
uspto-grants-1992_09
Patent number
US05149703

Reaction notes

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