Boron trifluoride etherate → 2-Butyl-2-(3,5-dimethoxy-phenyl)-[1,3]dithiolane

HRID 1376240

Reaction equation

HRID 1376240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH2:13][CH2:14][CH3:15])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.B(F)(F)F.CCOCC.[CH2:26]([SH:29])[CH2:27][SH:28]>C(Cl)Cl>[CH2:12]([C:11]1([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=2)[S:29][CH2:26][CH2:27][S:28]1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 2193883',5'-Dimethoxyvalerophenone

Product 1

HCID 3176902-Butyl-2-(3,5-dimethoxy-phenyl)-[1,3]dithiolaneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Compound 5 (3.52 g, 15.9 mmol) in anhydrous CH2Cl2 (58 ml); was added BF3-Et2O (0.58 ml, 4.8 mmol) and ethane-1,2-dithiol (2.71 g, 28.8 mmol) and stirred at room temperature for 16 h. The organic phase was then extracted with 10% NaOH (20 ml) followed by water and brine. The organic phase was dried, concentrated and the residue resolved over silica gel eluting with EtOAc/hexanes (5:10) to yield 4.50 g (95.2%) of Compound 9 as a colorless oil. Rf=0.51 (hexane:ethyl acetate 9:1); IR (neat) 2955, 1205, 1067 694 cm−1; 1H NMR δ 6.89 (d, J=2.22 Hz, 2H), 6.34 (t, J=2.21 Hz, 1H), 3.81 (s, 6H). 3.40–3.20 (m, 4H), 2.33 (t, J=7.53 2H), 1.31–1.20 (m, 4H), 0.85 (t, J=6.78 Hz, 3H). 13C NMR δ 160.56, 148.04, 106.01, 98.74, 74.58, 55.60, 45.92, 39.33, 30.23, 23.03, 14.13; MS: (ESI, Pos.) m/z 299 (M+).

Workup

  1. extractionThe organic phase was then extracted with 10% NaOH (20 ml)
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-171e6b7566584e80b09682e36b7d73d6
Source dataset
uspto-grants-2007_01
Patent number
US07169942B2

Linked notes

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