Tetrahydrofuran → HCID 20453410, compound

HRID 462294Notes

Reaction equation

HRID 462294 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-isocyanato4-(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-dd2a9cf70a3642e7afee0022f1e3b0de
Source dataset
uspto-grants-1977_12
Patent number
US04065573

Reaction notes

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