Triethylamine → HCID 19600040, compound

HRID 611305Notes

Reaction equation

HRID 611305 reaction equation
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)=[O:17].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:8]2[CH2:9][CH2:10][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:23])=[CH:20][CH:19]=1)=[O:17]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 19600157HCID 19600157, compound

Product 1

HCID 19600040HCID 19600040, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.165 g (1.034 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.25 g (1.1 mmol) of 4-(2-furoyl)benzoic acid and 0.58 ml (4.1 mmol) of triethylamine in 30 ml of dichloromethane, 0.19 ml (1.2 mmol) of diethyl cyanophosphonate was added dropwise at room temperature, followed by overnight stirring. This mixture was poured into aqueous sodium hydroxide and extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1) to yield the desired product.

Workup

  1. extractionextracted with ethyl acetate 3 times
  2. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1)

Sources & evidence

ORD record
ord-3c0cbf0d971c49cd90733708919957be
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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