Diethyl Ether → HCID 68328241, compound

HRID 2281195Notes

Reaction equation

HRID 2281195 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11](C(OCC)=O)[S:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:18][Mg]Br.C([O:23][CH2:24][CH3:25])C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:24]([OH:23])([CH3:25])[CH3:18])[S:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 68327941HCID 68327941, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68328241HCID 68328241, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (0° C.) solution of ethyl 3-(4-fluorophenyl)isothiazole-5-carboxylate (38.50 g, 153.2 mmol) in THF (400 mL) was added a solution of methylmagnesium bromide in diethyl ether (3.0 M, 128 mL, 384 mmol), dropwise over 20 minutes. After another 1.5 hours at 0° C. the reaction was quenched by the slow addition of ethyl acetate (20 mL) and concentrated. The residue was taken up in aqueous NH4Cl (400 mL) and extracted with ethyl acetate (2×150 mL). The combined extracts were dried (Na2SO4) and concentrated. The resulting amber syrup was purified by flash chromatography using a hexane/ethyl acetate gradient to afford 2-(3-(4-fluorophenyl)isothiazol-5-yl)propan-2-ol as soft, golden solid (29.02 g, 80%).

Workup

  1. customAfter another 1.5 hours at 0° C. the reaction was quenched by the slow addition of ethyl acetate (20 mL)
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate (2×150 mL)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting amber syrup was purified by flash chromatography

Sources & evidence

ORD record
ord-7433c9c60a1b4118abc3576bcaffcdc5
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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