Tetrahydrofuran → HCID 22561924, compound

HRID 983066Notes

Reaction equation

HRID 983066 reaction equation
C[C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1[CH:8]=[O:9].[CH2:10]1[CH2:14]O[CH2:12][CH2:11]1>O.C(O)(=O)C.C=O>[N:4]1([CH2:3][CH2:2][CH:6]2[CH2:5][CH2:7][CH2:7][C:5]3[NH:4][C:3]([CH:8]=[O:9])=[CH:2][C:6]2=3)[CH2:14][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 22561924HCID 22561924, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 712FormaldehydeSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3,5-dimethyl-1H-pyrrole-2-carbaldehyde (20 mmol) in THF (40 mL), water (20 mL), acetic acid (3 mL), formaldehyde (37% wt. % solution in water, 5 mL) and the appropriate amine (30 mL) was heated to reflux (oil bath 90-100° C.) for 6 hours. The reaction was concentrated to a volume of 30 mL, basified with 2N NaOH and extracted with ethyl acetate (2×150 mL) and DCM (4×100 mL). The combined organic layers were concentrated and the residue was purified on a silica gel column to give the desired product

Workup

  1. concentrationThe reaction was concentrated to a volume of 30 mL
  2. extractionextracted with ethyl acetate (2×150 mL) and DCM (4×100 mL)
  3. concentrationThe combined organic layers were concentrated
  4. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-6d58282df28e474992fe7c583a45b500
Source dataset
uspto-grants-2005_03
Patent number
US06861418B2

Reaction notes

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