Hydrochloric Acid → HCID 14157236, compound

HRID 1905337Notes

Reaction equation

HRID 1905337 reaction equation
[H-].[Na+].[C:3]([O:9][CH3:10])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].C([Li])CCC.[S:16]1[CH2:21][CH2:20][CH2:19][CH:18]([CH:22]=[O:23])[CH2:17]1.Cl>CCCCCC.O1CCCC1>[OH:23][CH:22]([CH:18]1[CH2:19][CH2:20][CH2:21][S:16][CH2:17]1)[CH2:7][C:5](=[O:6])[CH2:4][C:3]([O:9][CH3:10])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 11969521TETRAHYDROTHIOPYRAN-3-CARBOXALDEHYDEHCID 178418339Butyllithium

Product 1

HCID 14157236HCID 14157236, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

6.6 g of sodium hydride (80%) is added to 400 ml of tetrahydrofuran and the mixture is cooled to 0° C. At this temperature, 24.4 g of methyl acetoacetate is dripped in, the resulting mixture is stirred for 15 minutes, then 137.5 ml of a 1.6 molar butyllithium solution in hexane is dripped in and the mixture stirred for 30 minutes. At from 0° to 3° C., 26 g of tetrahydrothiopyran-3-carboaldehyde is dripped in and the mixture stirred for a further 30 minutes to complete the reaction. To this end, 45 ml of concentrated hydrochloric acid is carefully dripped in. The cold reaction mixture is poured into 250 ml of ice water and the organic phase is separated. The aqueous phase is extracted twice, each time with 250 ml of methyl tert-butyl ether. The combined organic extracts are washed once with 300 ml of saturated sodium chloride solution, dried with sodium sulfate and concentrated in a rotary evaporator. There is obtained 48.1 g of an oil which is used immediately for further reaction.

Workup

  1. stirringstirred for 30 minutes
  2. stirringstirred for a further 30 minutes
  3. customthe reaction
  4. customThe cold reaction mixture
  5. customthe organic phase is separated
  6. extractionThe aqueous phase is extracted twice
  7. washThe combined organic extracts are washed once with 300 ml of saturated sodium chloride solution
  8. dry with materialdried with sodium sulfate
  9. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-32361eab88de416e90f152d494ccceec
Source dataset
uspto-grants-1989_06
Patent number
US04842638

Reaction notes

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