Boron trifluoride etherate → HCID 10562396, compound

HRID 2175747Notes

Reaction equation

HRID 2175747 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13]([SH:16])[CH2:14][SH:15].B(F)(F)F.CCOCC>C(Cl)Cl>[S:15]1[C:2]2([CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]2)[S:16][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 10562396HCID 10562396, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a stirred solution of ethyl 4-oxocyclohexane carboxylate (5 g, 29.41 mmol) and ethane-1,2-dithiol (4.14 g, 44.11 mmol) in DCM (25 mL) was added BF3.Et2O (4.17 g, 29.41 mmol) at 0° C. and the reaction mixture was allowed to stir at 20-35° C. for 2 h. Then the reaction mixture was rotary evaporated under vacuum to get residue which was purified by column chromatography using mixture of 5% ethyl acetate/hexane as an eluent to get the desired compound as a yellow liquid (5.4 g, 75%); 1H NMR (400 MHz, DMSO-d6) δ 4.05 (q, J=7.4 Hz, 2H), 3.34-3.26 (m, 4H), 2.42-2.34 (m, 1H), 2.10-2.02 (m, 2H), 1.96-1.84 (m, 4H), 1.66-1.54 (m, 2H), 1.17 (t, J=7.3 Hz, 3H).

Workup

  1. customThen the reaction mixture was rotary evaporated under vacuum
  2. customto get residue which
  3. customwas purified by column chromatography
  4. additionmixture of 5% ethyl acetate/hexane as an eluent

Sources & evidence

ORD record
ord-bc2cbd56dd4946d082c7cf77c9ddb37c
Source dataset
uspto-grants-2015_06
Patent number
US09062075B2

Reaction notes

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