Tetrahydro-4H-pyran-4-ol → HCID 86211600, compound

HRID 2061249Notes

Reaction equation

HRID 2061249 reaction equation
[N:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:2]=[O:3].Cl.O1CCOCC1.[O:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1>ClCCl>[O:17]1[CH2:22][CH2:21][CH:20]([O:23][C:2]([NH:1][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:3])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 74956Tetrahydro-4H-pyran-4-olHCID 76283Ethyl isocyanatoacetateHCID 204431481,4-Dioxane hydrochloride

Product 1

HCID 86211600HCID 86211600, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.600 ml (4.80 mmol) of ethyl isocyanatoacetate was dissolved in dichloromethane. 0.06 ml of 4 N hydrochloric acid/1,4-dioxane solution was added to the obtained solution, and they were stirred at room temperature for 5 minutes. 0.503 ml (5.28 mmol) of tetrahydro-4H-4-pyranol was added to the reaction mixture, and they were stirred at room temperature overnight. After concentrating the reaction mixture under reduced pressure, the residue was purified by the silica gel chromatography (hexane:ethyl acetate=9:1 to 1:4), the title compound was obtained.

Workup

  1. stirringwere stirred at room temperature overnight
  2. concentrationAfter concentrating the reaction mixture under reduced pressure
  3. customthe residue was purified by the silica gel chromatography (hexane:ethyl acetate=9:1 to 1:4)

Sources & evidence

ORD record
ord-8ca8e6c411c74541ba364f0895b46665
Source dataset
uspto-grants-2012_10
Patent number
US08278329B2

Reaction notes

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