Boron trifluoride → 1-Methyl-1-[2-(formylamino)ethyl]-1,3,4,9-tetrahydroindeno[2,1-c]pyran

HRID 1731145Notes

Reaction equation

HRID 1731145 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.[CH:13]([NH:15][CH2:16][CH2:17][C:18](=O)[CH3:19])=[O:14].B(F)(F)F>C1C=CC=CC=1>[CH3:19][C:18]1([CH2:17][CH2:16][NH:15][CH:13]=[O:14])[C:2]2[CH2:1][C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[CH2:10][CH2:11][O:12]1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 113556481H-Indene-3-ethanolHCID 12375987N-(3-Oxobutyl)formamide

Product 1

HCID 214953281-Methyl-1-[2-(formylamino)ethyl]-1,3,4,9-tetrahydroindeno[2,1-c]pyran

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of indene-3-ethanol (1.6 g), 4-(formylamino)-2-butanone (1.2 g), described by H. Bredereck, et al., Chem. Ber., 2423 (1960), benzene (40 ml) and boron-trifluoride etherate (3 ml) is stirred at reflux temperature for 3 hr. The reaction mixture is washed with saturated sodium bicarbonate solution, dried and evaporated to dryness to afford the N-formyl derivative, 1-methyl-1-[2-(formylamino)ethyl]-1,3,4,9-tetrahydroindeno[2,1-c]pyran, nmr (CDCl)3 δ 3.3 (m, 4H), 6.5 (broad, 1H), 7.25 (m, 4H), 8.08 (s, 1H).

Workup

  1. temperatureat reflux temperature for 3 hr
  2. washThe reaction mixture is washed with saturated sodium bicarbonate solution
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-a4211fb8692e47d19ec8e10896e1d01e
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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