Hexachloroethane → HCID 66696615, compound

HRID 1672551Notes

Reaction equation

HRID 1672551 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][CH:12]=[N:11][C:10]=2[CH3:14])[CH:5]=[CH:6][C:7]=1[CH3:8].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:25]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1>[Cl:25][C:12]1[O:13][C:9]([C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([F:1])[CH:3]=2)=[C:10]([CH3:14])[N:11]=1

Participants

5

Reactant 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 66696660HCID 66696660, compound

Product 1

HCID 66696615HCID 66696615, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 30A (1.56 g, 8.16 mmol) in THF (36 mL) was cooled to −78° C., followed by dropwise addition of LiHMDS (1 M in THF, 10.2 mL, 10.2 mmol). The reaction was stirred 30 min and then hexachloroethane (3.86 g, 16.3 mmol) was added in one portion. The reaction was allowed to slowly warm to room temperature and stir over the weekend. The reaction was then quenched with 50 mL of 1:1 water:saturated aqueous NH4Cl solution, and extracted with Et2O (2×). The combined organic layer was dried with MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel (Analogix® SF40-80 g column) eluting with 7% EtOAc/hexanes to yield 1.71 g (93%) of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 7.43 (dd, J=11.9, 4.4 1H), 7.35-7.29 (m, 2H), 2.34 (s, 3H), 2.27 (d, J=1.9, 3H). MS (DCI+) m/z 226 (M+H).

Workup

  1. stirringstir over the weekend
  2. customThe reaction was then quenched with 50 mL of 1:1 water
  3. extractionsaturated aqueous NH4Cl solution, and extracted with Et2O (2×)
  4. dry with materialThe combined organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (Analogix® SF40-80 g column)
  8. washeluting with 7% EtOAc/hexanes

Sources & evidence

ORD record
ord-1b83396c6e3749458b7f9ee25476dc9f
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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