Tetrahydrofuran → HCID 67607880, compound

HRID 78745Notes

Reaction equation

HRID 78745 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]([C:7]1[CH2:11][CH2:10][O:9][CH:8]=1)=[O:6])[CH3:2].[Br:13]N1C(=O)CCC1=O.[O:21]1[CH2:25]CCC1>CO>[CH2:1]([O:3][C:4](=[O:12])[C:5]([C:7]1([Br:13])[CH2:11][CH2:10][O:9][CH:8]1[O:21][CH3:25])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 11571862HCID 11571862, compound

Product 1

HCID 67607880HCID 67607880, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-2.5 °C

Procedure

Ethyl-2-(4,5-dihydrofuran-3-yl)-2-oxoacetate (45 g) was dissolved in tetrahydrofuran (225 ml) and Methanol (45 ml). The reaction mass was cooled to −5 to 0° C. N-bromosuccinimide (47 g) was added lot wise by maintaining temp below 0° C. Reaction mass was then stirred at 20-25° C. for 12 hrs. Reaction mass was concentrated to residue under vacuum at 40° C. Residue was dissolved in Ethyl acetate (450 ml) and washed with sodium sulphite solution (10%, 2×135 ml). Reaction mass was then concentrated to residue to get ethyl-2-(3-bromo-2-methoxytetrahydrofuran-3-yl)-2-oxoacetate (Yield 63 g).

Workup

  1. temperatureby maintaining temp below 0° C
  2. customReaction mass
  3. customReaction mass
  4. concentrationwas concentrated to residue under vacuum at 40° C
  5. dissolutionResidue was dissolved in Ethyl acetate (450 ml)
  6. washwashed with sodium sulphite solution (10%, 2×135 ml)
  7. customReaction mass
  8. concentrationwas then concentrated to residue

Sources & evidence

ORD record
ord-ed53fd13716f4c4797a5d3dd11b6677c
Source dataset
uspto-grants-2014_09
Patent number
US08841467B2

Reaction notes

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