Hydrochloric Acid → HCID 14770244, compound

HRID 2291743Notes

Reaction equation

HRID 2291743 reaction equation
[CH:1]([C:3]1[C:19]2[CH:18]=[C:17](C(OCC)=O)[O:16][C:15]=2[C:14]2[CH:13]=[CH:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]=2[CH:4]=1)=[O:2].[OH-].[Na+].C1COCC1.Cl>O>[CH:18]1[C:19]2[C:3]([CH:1]=[O:2])=[CH:4][C:5]3[C:6]4[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=4[CH:12]=[CH:13][C:14]=3[C:15]=2[O:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14770243HCID 14770243, compound

Product 1

HCID 14770244HCID 14770244, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a RB flask equipped with magnetic stirring bar, condenser, and N2 inlet line with bubbler was added ethyl 11-formyl-phenanthro[1,2-b]furan-2-carboxylate (15A, 2.5 g. 7.8 mmol), 1N NaOH solution (25 mL), THF (50 mL) and H2O (25 mL). The mixture was refluxed for 2 h until it became homogeneous. The mixture was acidified with 1N HCl and the solvent removed by rotary evaporation. The crude solid was then heated to 150° with copper powder (0.9 g) and quinoline (Aldrich, 25 mL) for 1 h. The reaction mixture was cooled and the quinoline removed under vacuum to give a crude dark green solid. After chromatography and crystallization (CH2Cl2 /hexane) 0.71 g (37% yield) of phenanthro[1,2-b]furan-11-carbaldehyde, mp 145°-150°, (C,H).

Workup

  1. customTo a RB flask equipped with magnetic stirring bar, condenser, and N2 inlet line with bubbler
  2. temperatureThe mixture was refluxed for 2 h until it
  3. customthe solvent removed by rotary evaporation
  4. temperatureThe crude solid was then heated to 150° with copper powder (0.9 g) and quinoline (Aldrich, 25 mL) for 1 h
  5. temperatureThe reaction mixture was cooled
  6. customthe quinoline removed under vacuum
  7. customto give a crude dark green solid

Sources & evidence

ORD record
ord-bd5e315194924427931b792deb780db8
Source dataset
uspto-grants-1989_01
Patent number
US04797495

Reaction notes

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