Hexachloroethane → HCID 178455355, compound

HRID 2095670Notes

Reaction equation

HRID 2095670 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH:19]=[C:18]([I:20])[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.C1CCCCC1.[Cl:35]C(Cl)(Cl)C(Cl)(Cl)Cl.[NH4+].[Cl-]>C1COCC1>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[C:19]([Cl:35])=[C:18]([I:20])[CH:17]=[N:16]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

7

Reactant 5

HCID 6214HexachloroethaneHCID 8078CyclohexaneHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 667595941H-Pyrazole, 1-[trans-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]cyclohexyl]-4-iodo-

Product 1

HCID 178455355HCID 178455355, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-[4-(tert-butyldimethylsilyloxy)cyclohexyl]-4-iodo-1H-pyrazole (50.0 mg, 0.123 mmol) in THF (3 mL, 40 mmol) was cooled to −78° C. and added 1.5 M of LDA in cyclohexane (0.107 mL, 0.160 mmol). After stirring for 5 min, a solution of hexachloroethane (35.0 mg, 0.148 mmol) in THF was added, and the mixture was stirred at −78° C. for 30 min. Sat. NH4Cl was added to quench, and the organic solvent was removed in vacuo. The material was extracted with DCM and water, and the organic layer was dry-loaded onto silica gel for column chromatography, eluting with 1-3% EtOAc/heptane. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a clear oil. 1H NMR (400 MHz, CD3OD): δ=0.11 (s, 6H), 0.93 (s, 9H), 1.46-1.60 (m, 2H), 1.88-2.08 (m, 6H), 3.69-3.80 (m, 1H), 4.32-4.43 (m, 1H), 7.58 (s, 1H).

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 min
  2. customto quench
  3. customthe organic solvent was removed in vacuo
  4. extractionThe material was extracted with DCM and water
  5. washeluting with 1-3% EtOAc/heptane
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-b5d111e1f56a4abba942a67dbaa095a2
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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