Triethylamine → HCID 19600102, compound

HRID 611300Notes

Reaction equation

HRID 611300 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.[C:11]1([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=[O:17])[S:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[C:11]1([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([N:8]3[CH2:9][CH2:10][C:5]4[CH:4]=[CH:3][O:2][C:6]=4[CH2:7]3)=[O:23])=[CH:20][CH:19]=2)=[O:17])[S:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 196000994-(2-Thenoyl)benzoic acid

Product 1

HCID 19600102HCID 19600102, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.173 g (1.084 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.38 g (1.6 mmol) of 4-(2-thenoyl)benzoic acid and 0.60 ml (4.3 mmol) of triethylamine in 30 ml of dichloromethane, 0.25 ml (1.6 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-928a8a5151d94bd1a35ba129eeefdae8
Source dataset
uspto-grants-1999_12
Patent number
US05998433

Reaction notes

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