Hydrochloric Acid → HCID 9798661, compound

HRID 1017732Notes

Reaction equation

HRID 1017732 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]2[O:15][C:16]([CH:18]=[O:19])=[CH:17][C:7]1=2.C1COCC1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[Cl:23])[CH2:5][N:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]2[O:15][C:16]([CH2:18][OH:19])=[CH:17][C:7]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 18405228HCID 18405228, compound

Product 1

HCID 9798661HCID 9798661, compoundYield 114.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(3,4-dichlorobenzyl)-2-formylfuro[3,2-b]pyrrole-5-carboxylate (0.2 g) was dissolved in methanol (10 mL) and THF (10 mL) and cooled to 0° C. Sodium borohydride (26 mg) was added and the reaction stirred for 2 hours. The mixture was acidified with 2M HCl, partially evaporated, and extracted with ethyl acetate. Combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a white solid (0.23 g), NMR d(CDCl3) 3.8 (3H, s), 4.65 (2H, d), 5.6 (2H, s), 6.2 (1H, s), 6.85 (1H, s), 7.0 (1H, dd), 7.2 (1H, d), 7.35 (1H, d); M/z (+) 340 (MH+), 332, 278.

Workup

  1. custompartially evaporated
  2. extractionextracted with ethyl acetate
  3. dry with materialCombined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cca3a6e15323471aae251c152232df06
Source dataset
uspto-grants-2002_11
Patent number
US06479527B1

Reaction notes

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