Tetrahydrofuran → naphthalen-2-ylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylate

HRID 1095702Notes

Reaction equation

HRID 1095702 reaction equation
[C:1](Cl)(=[O:14])[O:2][CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=1.[NH:16]1[CH2:20][CH:19]=[CH:18][CH2:17]1.C1COCC1>C([O-])(O)=O.[Na+]>[N:16]1([C:1]([O:2][CH2:3][C:4]2[CH:13]=[CH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=2)=[O:14])[CH2:20][CH:19]=[CH:18][CH2:17]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 660593-PyrrolineHCID 15764399(Naphthalen-2-yl)methyl carbonochloridate

Product 1

HCID 66781493naphthalen-2-ylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent2×

Procedure

Naphthalen-2-ylmethyl carbonochloridate (31.93 g, 144.7 mmol) was added to a solution of 2,5-dihydro-1H-pyrrole (10 g, 144.7 mmol) in a 1:1 mixture of saturated NaHCO3 (400 mL) and THF (400 mL). The reaction was stirred for 12 hours, condensed to a small volume, diluted with saturated NaHCO3, extracted with CH2Cl2, wash with 1 N HCl, dried over sodium sulfate, filtered and condensed to afford 27.5 g of the desired product as a solid.

Workup

  1. customcondensed to a small volume
  2. extractionextracted with CH2Cl2
  3. washwash with 1 N HCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customcondensed

Sources & evidence

ORD record
ord-b4c9e0dc253c4a01869412b143a098f8
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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