Ammonium Chloride → ethyl (E)-4-hydroxy-4-(2-thiophen-2-yl-benzoxazol-6-yl)but-2-enoate

HRID 1619999Notes

Reaction equation

HRID 1619999 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH:15]=[O:16])[CH:12]=[CH:11][C:9]=2[N:10]=1.I/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21].[Cl-].[NH4+]>CS(C)=O.[Cl-].[Cr+2].[Cl-].[Ni](Cl)Cl>[OH:16][CH:15]([C:13]1[CH:12]=[CH:11][C:9]2[N:10]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[O:7][C:8]=2[CH:14]=1)/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 639791Ethyl 3-iodo-2E-acrylateHCID 820366102-Thiophen-2-yl-benzoxazole-6-carbaldehyde

Product 1

HCID 67464612ethyl (E)-4-hydroxy-4-(2-thiophen-2-yl-benzoxazol-6-yl)but-2-enoate

Reagents, catalysts & solvents 3

HCID 24385Nickel DichlorideCatalystHCID 10197677chromium(II) dichlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1.2 g (5.23 mmol) 2-thiophen-2-yl-benzoxazole-6-carbaldehyde and 2.5 g (11.06 mmol) ethyl (E)-3-iodoacrylate in DMSO is added dropwise at RT to 4.0 g (32.55 mmol) chromium-(II)-chloride and 10 mg (0.08 mmol) nickel-(II)-chloride. The reaction mixture is stirred overnight at RT, then combined with sat. ammonium chloride solution and extracted 3× with DCM. The combined org. phases are concentrated by rotary evaporation i. V. and the residue is purified on silica gel (eluant: cyclohexane/EA).

Workup

  1. extractionextracted 3× with DCM
  2. concentrationphases are concentrated by rotary evaporation i
  3. customand the residue is purified on silica gel (eluant: cyclohexane/EA)

Sources & evidence

ORD record
ord-f711ece1cda54e21b1199015a4384fb7
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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