Hexachloroethane → HCID 66696653, compound

HRID 1672555Notes

Reaction equation

HRID 1672555 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][O:5][C:6]=1[C:7]1[CH2:12][CH2:11][C@@H:10]([C:13]([CH3:15])=[CH2:14])[CH2:9][CH:8]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:26]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CCOCC>[Cl:26][C:4]1[O:5][C:6]([C:7]2[CH2:12][CH2:11][C@@H:10]([C:13]([CH3:15])=[CH2:14])[CH2:9][CH:8]=2)=[C:2]([CH3:1])[N:3]=1

Participants

6

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 66696612HCID 66696612, compound

Product 1

HCID 66696653HCID 66696653, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 32A (0.55 g, 2.7 mmol) in THF (20 mL) at −78° C. was added LiHMDS (1 M in THF, 3.25 mL, 3.25 mmol) dropwise over a period of 6-8 min. After 30 min hexachloroethane (1.28 g, 5.41 mmol) was added at once as a solid and the mixture was left to stir overnight warming to ambient temperature. The mixture was diluted with Et2O and washed with aqueous NH4Cl solution and water. The organic layer was separated and concentrated in vacuo, and the residue chromatographed on silica gel with EtOAc/hexanes (0%-20%) to yield 0.47 g (73%) of the title compound as an oil. 1H NMR (300 MHz, DMSO-d6) δ 6.11 (m, 1H), 4.74 (m, 2H), 2.48-2.24 (m, 3H), 2.23-2.00 (m, 5H), 1.92-1.82 (m, 1H), 1.73 (s, 3H), 1.57-1.41 (m, 1H). MS (ESI+) m/z 238 (M+H).

Workup

  1. waitthe mixture was left
  2. washwashed with aqueous NH4Cl solution and water
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on silica gel with EtOAc/hexanes (0%-20%)

Sources & evidence

ORD record
ord-d5afbf02346f45a586403d816d0b82a1
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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