Epichlorohydrin → HCID 87367383, compound

HRID 1676138Notes

Reaction equation

HRID 1676138 reaction equation
[CH2:1]([C:5]1[C:6]([CH3:24])=[C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:20]=[C:19]([CH3:21])[C:18]([OH:22])=[C:17]([CH3:23])[CH:16]=3)[N:11]=2)[S:8][CH:9]=1)[CH:2]([CH3:4])[CH3:3].[CH2:25]([CH:27]1[O:29][CH2:28]1)Cl>C(O)(C)C.[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>[CH3:23][C:17]1[CH:16]=[C:15]([C:12]2[N:11]=[C:10]([C:7]3[S:8][CH:9]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]=3[CH3:24])[O:14][N:13]=2)[CH:20]=[C:19]([CH3:21])[C:18]=1[O:22][CH2:25][CH:27]1[CH2:28][O:29]1

Participants

6

Reactant 2

HCID 7835Epichlorohydrin2×HCID 136133433HCID 136133433, compound

Product 1

HCID 87367383HCID 87367383, compoundYield 63.9%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 10340Sodium CarbonateSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-[5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenol (515 mg, 1.50 mmol) in isopropanol (20 mL), 3 N aq. NaOH (5 mL) followed by epichlorohydrine (473 mg, 5.12 mmol) is added and the mixture is stirred at rt for 15 h. Another portion of epichlorohydrine (473 mg, 5.12 mmol) is added and stirring is continued for 24 h. The mixture is diluted with sat. aq. Na2CO3 and is then extracted with DCM (4×75 mL). The combined organic extracts are dried (Na2SO4), filtered and evaporated. The residue is purified by CC on silica gel eluting with heptane:EA 4:1 to give rac-3-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-5-(4-isobutyl-3-methyl-thiophen-2-yl)-[1,2,4]oxadiazole (382 mg) as a white powder; LC-MS: tR=1.22 min, [M+1]=399.28.

Workup

  1. additionis added
  2. stirringstirring
  3. waitis continued for 24 h
  4. extractionis then extracted with DCM (4×75 mL)
  5. dry with materialThe combined organic extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by CC on silica gel eluting with heptane:EA 4:1

Sources & evidence

ORD record
ord-ae5a68027cc5416f9325df188f66b990
Source dataset
uspto-grants-2011_08
Patent number
US08003800B2

Reaction notes

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