Tetrahydrofuran → HCID 20453410, compound

HRID 1448554Notes

Reaction equation

HRID 1448554 reaction equation
C1O[C:4]2([CH2:9][CH2:8][C:7]([N:15]=[C:16]=O)([C:10]3[S:11][CH:12]=[CH:13][CH:14]=3)[CH2:6][CH2:5]2)[O:3]C1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O>[CH3:16][NH:15][C:7]1([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 12595566HCID 12595566, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20453410HCID 20453410, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 2.21 g. (8.3 mmole) of 4-isocyanato-4-(2-thienyl)cyclohexanone ethylene ketal in 40 ml. tetrahydrofuran (THF) is added to a suspension of 0.32 g. (8.4 mmole) of lithium aluminum hydride (LAH) in 5 ml. THF. Following 4 hours' stirring under reflux the mixture is cooled in ice. There is then added in turn 0.32 ml. water, 0.32 ml. 15% NaOH and 0.96 ml. water. The inorganic gel is collected on a filter and the filtrate taken to dryness. A solution of the residue in a small amount of ether is treated with a just-sufficient amount of 3 N hydrogen chloride in ether. The precipitated salt is recrystallized from methylene chloride:ethyl acetate to afford 0.84 g. (35% yield) of 4-methylamino-4-(2-thienyl)cyclohexanone, ethylene ketal hydrochloride, m.p. 211°-214° C.

Workup

  1. temperatureunder reflux the mixture
  2. temperatureis cooled in ice
  3. additionThere is then added in turn 0.32 ml
  4. customThe inorganic gel is collected on
  5. filtrationa filter
  6. additionA solution of the residue in a small amount of ether is treated with a just-sufficient amount of 3 N hydrogen chloride in ether
  7. customThe precipitated salt is recrystallized from methylene chloride
  8. customethyl acetate to afford 0.84 g

Sources & evidence

ORD record
ord-aeddcdd84a69465982449af891b1a9a3
Source dataset
uspto-grants-1979_12
Patent number
US04180584

Reaction notes

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