tert-Butyldimethylsilyl chloride → 8-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-3,8-dimethyl-

HRID 370517Notes

Reaction equation

HRID 370517 reaction equation
[Li][C:2]1([CH3:13])[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.[Si]([N:21]=[C:22]=S)(C(C)(C)C)(C)C.[Si](Cl)(C(C)(C)C)(C)C>C1COCC1>[C:22]([C:2]1([CH3:13])[C:11]2[N:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1)#[N:21]

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 13272319tert-Butyl(isothiocyanato)dimethylsilaneHCID 178506693HCID 178506693, compound

Product 1

HCID 123519318-Quinolinecarbonitrile, 5,6,7,8-tetrahydro-3,8-dimethyl-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5,6,7,8-tetrahydro-8-lithio-3,8-dimethylquinoline (20 mM) was generated as described in Example 2 and allowed to react with t-butyldimethylsilyl isothiocyanate (20 mM) as described in Example 2. After 0.5 hours a solution of t-butyldimethylsilyl chloride (3.1 g, 20 mM) in THF (10 ml) was added and the mixture allowed to stand for 16 hours at ambient temperature. The reaction was quenched with 2N hydrochloric acid (50 ml). After 1 hour the aqueous layer was separated, basified (to pH9) and extracted with dichloromethane (2×50 ml) and the organic extracts were dried and evaporated. Kugelrohr distillation of the residue gave the nitrile title compound. (2.8 g, 75%) bp. 90°/0.01 mm (bath temp.)

Workup

  1. customThe reaction was quenched with 2N hydrochloric acid (50 ml)
  2. customAfter 1 hour the aqueous layer was separated
  3. extractionextracted with dichloromethane (2×50 ml)
  4. customthe organic extracts were dried
  5. customevaporated
  6. distillationKugelrohr distillation of the residue

Sources & evidence

ORD record
ord-745d75fdb1864da893bc3baf02f30265
Source dataset
uspto-grants-1985_07
Patent number
US04526970

Reaction notes

Loading…