Diethyl Ether → HCID 68328263, compound

HRID 2281233Notes

Reaction equation

HRID 2281233 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4](C(OCC)=O)[CH:3]=1.[CH3:12][Mg]Br.C([O:17][CH2:18][CH3:19])C>C1COCC1>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:18]([OH:17])([CH3:19])[CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 15293216Ethyl 5-bromothiophene-3-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 68328263HCID 68328263, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and cooled (0° C.) solution of ethyl 5-bromothiophene-3-carboxylate (13.30 g, 56.57 mmol) in THF (100 mL) was added a solution of methylmagnesium bromide in diethyl ether [3.0 M] (55.0 mL, 165 mmol), dropwise over 20 minutes. After 2 hours, the reaction solution was concentrated. The residue was taken up in aqueous NH4Cl (200 mL) and extracted with ethyl acetate (2×100 mL). The combined extracts were dried (Na2SO4) and concentrated. The resulting amber oil was purified by flash chromatography using a hexane/ethyl acetate gradient to afford 2-(5-bromothiophen-3-yl)propan-2-ol as a pale amber oil (8.05 g, 64%).

Workup

  1. waitAfter 2 hours
  2. concentrationthe reaction solution was concentrated
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe resulting amber oil was purified by flash chromatography

Sources & evidence

ORD record
ord-f5e6dbdebd614cc1b22c4ce540f66f7a
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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