Boron trifluoride etherate → HCID 15723560, compound

HRID 979817Notes

Reaction equation

HRID 979817 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)C=C.[CH2:13]1[C:22]2C(=CC=CC=2)CC[CH2:14]1.B(F)(F)F.CCOCC>>[CH2:22]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[NH:4][CH2:5][CH2:6]2)[CH:13]=[CH2:14]

Participants

4

Reactant 3

HCID 8000Boron trifluoride etherateHCID 8404TetralinHCID 132646611-(Prop-2-en-1-yl)-2,3-dihydro-1H-indole

Product 1

HCID 15723560HCID 15723560, compoundYield 77%

Conditions

Temperature
200 °C

Procedure

A mixture of 2,3-dihydro-1-(2-propenyl)-1H-indole (1.59 g), tetralin (25 ml) and borontrifluoride etherate (1.3 ml) was heated at 200° C. for 1.5 hours. The reaction mixture was cooled to room temperature then quenched with 10% sodium carbonate and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried and evaporated. The residue was chromatographed over silica (ethyl acetate-hexane 15:85) affording 1.23 g of the desired product (77% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthen quenched with 10% sodium carbonate
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed over silica (ethyl acetate-hexane 15:85)

Sources & evidence

ORD record
ord-69154a66a0a648f48a296095e35e984a
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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