Tetrahydrofuran → HCID 66917857, compound

HRID 2215807Notes

Reaction equation

HRID 2215807 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[CH:7]([C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)=O.C1C[O:21][CH2:20][CH2:19]1>>[NH:16]1[C:17]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[CH:7]=[CH:19][C:20]([O:4][CH2:2][CH3:5])=[O:21])[CH:14]=[CH:15]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 2734629Indole-7-carboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 66917857HCID 66917857, compoundYield 80%

Procedure

A 1.0 M solution of potassium tert-butoxide in THF (12.0 mL, 12.0 mmol) was added to THF (50 mL) at −78° C. under N2 followed by triethyl_phosphonoacetate (2.6 mL, 13.1 mmol). A solution of 7-formylindole (1.01 g, 7.0 mmol) in THF (10 mL) was then added dropwise over 5 min. The resulting red solution was stirred for 2 h, quenched with saturated NaHCO3 (50 mL) and extracted with EtOAc (100 mL). The organic layer was washed with H2O (60 mL), brine (60 mL), dried (MgSO4) and concentrated to a brown oil. Flash chromatography (SiO2, 8%EtOAc/hexanes containing 2% TEA) gave the title compound (1.0 g, 80%) as a white solid. 1H NMR (300 MHz, CDCl3) 8.53 (bs, 1H), 7.98 (m, 1H), 7.71 (m, 1H), 7.42 (m, 1H), 7.27 (m, 1H), 7.14 (m, 1H), 6.60 (m, 1H), 6.51 (m, 1H), 4.31 (m, 2H), 1.40 (m, 3H).

Workup

  1. customquenched with saturated NaHCO3 (50 mL)
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with H2O (60 mL), brine (60 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated to a brown oil

Sources & evidence

ORD record
ord-bd9f9b5439494465983afbf4c159fec0
Source dataset
uspto-grants-2006_09
Patent number
US07109229B2

Reaction notes

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