Bromide ion → HCID 57437552, compound

HRID 1986667Notes

Reaction equation

HRID 1986667 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8]CC)=O)=[CH:2]1.[Br-].S(=O)(=O)(O)O.[CH2:17](OCC)[CH3:18]>>[O:1]1[CH:5]=[CH:4][C:3]([C:6]2([OH:8])[CH2:18][CH2:17]2)=[CH:2]1

Participants

5

Reactant 4

HCID 259Bromide ionHCID 1118Sulfuric AcidHCID 3283Diethyl Ether2×HCID 69201Ethyl 3-furoate

Product 1

HCID 57437552HCID 57437552, compound

Procedure

2.50 g (17.84 mmol) ethyl furan-3-carboxylate and 0.53 ml (1.82 mmol) titanium tetra-isopropyloxide are placed in 56 ml diethyl ether, 12.61 ml (37.82 mmol) ethylmagnesum bromide (Grignard reagent in tetrahydrofuran) in 28 ml diethyl ether are added dropwise within 1 hour, while the temperature should not rise above 20° C. The reaction mixture is stirred for 1.5 hours, then hydrolysed with 180 ml 10% sulphuric acid. The aqueous phase is extracted with diethyl ether, the combined organic phases are dried and evaporated to dryness. The residue is purified by chromatography. Yield: 1.05 g (47% of theoretical)

Workup

  1. customrise above 20° C
  2. extractionThe aqueous phase is extracted with diethyl ether
  3. customthe combined organic phases are dried
  4. customevaporated to dryness
  5. customThe residue is purified by chromatography

Sources & evidence

ORD record
ord-5cbe3340c8184e2fb77e5f398df2f525
Source dataset
uspto-grants-2009_06
Patent number
US07550472B2

Reaction notes

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