Water → 2-Hydroxypropoxy(a-niline] methylenmalonate

HRID 441119Notes

Reaction equation

HRID 441119 reaction equation
[CH2:1]1[O:4][CH:2]1[CH3:3].C([N:7](CC)[C:8]1[CH:13]=[CH:12][C:11](F)=[C:10](F)[C:9]=1O)C.[CH2:19]=[C:20]([C:24]([O-:26])=[O:25])[C:21]([O-:23])=[O:22].O>C1COCC1>[OH:22][CH:2]([CH3:3])[CH2:1][O:4][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:19]=[C:20]([C:24]([O-:26])=[O:25])[C:21]([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 6378Propylene OxideHCID 86749519Diethyl (3,4-difluoro-2-hydroxyaniline) methylenmalonate

Product 1

HCID 867495202-Hydroxypropoxy(a-niline] methylenmalonateYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2,9 mgr (0,06 mmol) of HNa at 60%, 161 mgr (1,26 mmol) of LiClO4 anhydrous and 51 ml (0,32 mmol) of propylene oxide are added to a solution of 100 mgr) 0,32 mmol) of the compound [4] in 0,33 ml of THF. The reaction mixture is heated at 40° C. for two days and then 2 ml of water are added. The aqueous layer is extracted with ACOEt, ethyl acetate, (2×5 ml). The combination of the organic layers is dried with MgSO4 and the solvent is eliminated thus obtaining 77 mgr (65%) of the desired product [5].

Workup

  1. extractionThe aqueous layer is extracted with ACOEt, ethyl acetate, (2×5 ml)
  2. dry with materialThe combination of the organic layers is dried with MgSO4

Sources & evidence

ORD record
ord-7a33f4a562e742a799b5778a80e31a7e
Source dataset
uspto-grants-1996_05
Patent number
US05521310

Reaction notes

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