Boron trifluoride → HCID 57801118, compound

HRID 1817681Notes

Reaction equation

HRID 1817681 reaction equation
[C:1]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1C(=O)CCCC=C.[CH:20]([SH:24])([SH:23])[CH2:21][CH3:22].B(F)(F)F.[OH-].[Na+]>C(Cl)Cl>[C:14]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:15]=[CH:16][C:17]([C:20]2([CH2:21][CH2:22][CH2:6][CH:1]=[CH2:2])[S:24][CH2:5][CH2:4][CH2:3][S:23]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 64285461,1-PropanedithiolHCID 69047929HCID 69047929, compound

Product 1

HCID 57801118HCID 57801118, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Biphenylyl-hex-5-en-1-one (1.5 g) was dissolved in DCM (30 ml). Propanedithiol (1.5 g) and boron trifluoride dietherate (1 ml) were added and the mixture stirred for 24 h. 5% NaOH (50 ml) was added and the mixture separated. The organic phase was washed with water, dried and evaporated to give an oil. Column chromatography (petrol/ethyl acetate) gave the title compound as a thick oil. δC (CDCl3, 62.9 MHz): 23.2, 25.3, 27.7, 33.6, 44.6, 58.9, 115.0, 127.1, 127.1, 127.4, 128.8, 129.4, 138.1, 139.6, 140.5 and 141.0. δH (CDCl3, 250 MHz): 1.40 (2H, m), 2.00 (6H, m), 2.70 (4H, m), 4.92 (2H, m), 5.68 (1H, m), 7.34 (1H, m), 7.44 (2H, m), 7.62 (4H, m) and 7.96 (2H, d, J 8.2).

Workup

  1. customthe mixture separated
  2. washThe organic phase was washed with water
  3. customdried
  4. customevaporated
  5. customto give an oil

Sources & evidence

ORD record
ord-1715188406504100beac5bb8825fdc1e
Source dataset
uspto-grants-2009_10
Patent number
US07598289B2

Reaction notes

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