Tetrahydrofuran → HCID 18788311, compound

HRID 1106454Notes

Reaction equation

HRID 1106454 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[N:9]([C:10]=1[CH:11]=[O:12])[C:8](=[O:13])[C:7]1[C:14]([OH:22])=[C:15]([CH2:19][CH2:20][CH3:21])[C:16]([OH:18])=[CH:17][C:6]=1[O:5]2.C1COCC1.[BH4-].[Na+]>CCO.O.C(OCC)(=O)C.Cl>[OH:12][CH2:11][C:10]1[N:9]2[C:4]([O:5][C:6]3[CH:17]=[C:16]([OH:18])[C:15]([CH2:19][CH2:20][CH3:21])=[C:14]([OH:22])[C:7]=3[C:8]2=[O:13])=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 15463648HCID 15463648, compound

Product 1

HCID 18788311HCID 18788311, compoundYield 150.8%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 40 mg (0.11 mmol) of 2-chloro-6,8-dihydroxy-9-oxo-7-propyl-9H-pyrrolo[2,1-b][1,3]benzoxazine-1-carboxaldehyde made by the process of Example 9 in 4 mL of EtOH and 4 mL THF was added 20 mg of sodium borohydride. After 15 min the mixture was diluted with H2O and ethyl acetate and 1 mL of 1 N HCl with vigorous bubbling. The mixture was extracted with ethyl acetate and the organic layer dried (Na2SO4) and concentrated to give 48 mg of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c5f9bbdb27984103b1f622844594cecb
Source dataset
uspto-grants-2000_05
Patent number
US06057315

Reaction notes

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