Bromocyclopropane → HCID 17977197, compound

HRID 330296Notes

Reaction equation

HRID 330296 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.C1(Br)CC1.[Mg].[CH3:11][O:12][C:13]1[CH:26]=[CH:25][C:16]2[N:17]3[CH:22]=[C:21]([CH:23]=[O:24])[N:20]=[C:18]3[S:19][C:15]=2[CH:14]=1>>[CH3:11][O:12][C:13]1[CH:26]=[CH:25][C:16]2[N:17]3[CH:22]=[C:21]([CH:23]([CH:1]4[CH2:2][CH2:3]4)[OH:24])[N:20]=[C:18]3[S:19][C:15]=2[CH:14]=1

Participants

5

Reactant 4

HCID 78037BromocyclopropaneHCID 5462224MagnesiumHCID 11287703HCID 11287703, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 17977197HCID 17977197, compoundYield 69%

Procedure

A mixture of 3.6 g (0.03 mole) of cyclopropyl magnesium bromide prepared from cyclopropyl bromide and 0.8 g (0.033 mole) of magnesium in 50 ml of dry T.H.F. was added dropwise to a suspension of 3.9 g (0.0177 mole) of 7-methoxy-imidazo[2,1-b]benzothiazole-2carboxaldehyde in 80 ml of dry T.H.F. The mixture was stirred at room temperature for 3 hours and was quenched with saturated aqeous ammonium chloride solution. The mixture was extracted with ethyl acetate and the extracts were dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel and eluted with 2% methanol/dichloromethane to obtain 2.75 g (69% yield) of [7-methoxy-imidazo[2,1-b]benzothiazol-2-yl) cyclopropyl methanol as colorless solid melting at 151° to 153° C.

Workup

  1. customwas quenched with saturated aqeous ammonium chloride solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe extracts were dried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluted with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-fd964b8ed8e6406389fe8916f71f6b52
Source dataset
uspto-grants-1990_01
Patent number
US04895863

Reaction notes

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