Boron trifluoride etherate → HCID 69198031, compound

HRID 268666Notes

Reaction equation

HRID 268666 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][OH:13].B(F)(F)F.CCOCC.[C:23]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])(=O)[CH2:24][CH3:25]>ClCCl>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][C:23]1([CH2:24][CH3:25])[C:6]2[NH:7][C:8]3[C:4]([C:5]=2[CH2:11][CH2:12][O:13]1)=[CH:3][C:2]([CH3:1])=[CH:10][CH:9]=3)[CH3:32]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 78656Ethyl 3-oxovalerateHCID 12272816HCID 12272816, compound

Product 1

HCID 69198031HCID 69198031, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(5-methyl-1H-indol-3-yl)-ethanol (0.48 g, 2.7 mmol) in dichloromethane (10 mL) was added boron trifluoride diethyl etherate (0.468 g, 3.3 mmol), followed by ethyl propionylacetate (0.649 g, 4.5 mmol). The mixture was stirred at room temperature for 5 hours. It was quenched with saturated sodium bicarbonate solution and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated to dryness. Flash chromatography on silica gel provided 0.421 g (52%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3) δ 8.90 (br, 1H), 7.28 (s, 1H), 7.24 (d, 1H), 6.99 (d, 1H), 4.16 (m, 2H), 4.03 (m, 1H), 3.94 (m, 1H), 2.98 (d, 1H), 2.88 (d, 1H), 2.80 (m, 1H), 2.73 (m, 1H), 2.44 (s, 3H), 2.12 (m, 1H), 1.98 (m, 1H), 1.25 (t, 3H), 0.80 (t, 3H); ESI (−) MS m/e=300 (MH−).

Workup

  1. customIt was quenched with saturated sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a64459fb4fa94468ad2df8c22f45fa76
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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