Hydrochloric Acid → HCID 53704353, compound

HRID 342421Notes

Reaction equation

HRID 342421 reaction equation
[BH4-].[Na+].[N+:3]([C:6]1[C:14]2[O:13][C:12]3[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[C:11]=3[C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl>C(O)C.CN(C)C=O.O>[OH:19][CH:18]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[C:14]=3[O:13][C:12]=2[CH2:15][CH2:16][CH2:17]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 53926227HCID 53926227, compound

Product 1

HCID 53704353HCID 53704353, compoundYield 75.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium borohydride (38 mg) was added to a solution of 6-nitro-1-oxo-1,2,3,4-tetrahydrodibenzofuran (231 mg) in a mixture of ethanol (1.5 ml) and N,N-dimethylformamide (1.5 ml). The mixture was stirred at ambient temperature for 20 minutes, diluted with water and acidified with 3.6% hydrochloric acid. The separated oil was extracted with ethyl acetate and the extract was washed with aqueous saturated sodium bicarbonate and brine, dried over sodium sulfate and concentrated in vacuo. The residue was crystallized from diisopropyl ether to give 1-hydroxy-6-nitro-1,2,3,4-tetrahydrodibenzofuran (175 mg).

Workup

  1. extractionThe separated oil was extracted with ethyl acetate
  2. washthe extract was washed with aqueous saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-506d8a9a5b7f4a6db39866677e467640
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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