3-Furancarboxaldehyde, tetrahydro- → HCID 72305307, compound

HRID 1972275Notes

Reaction equation

HRID 1972275 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH:6]=O)[CH2:2]1.[ClH:8].[NH2:9][OH:10]>C(O)C>[OH:10][N:9]=[C:6]([Cl:8])[CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1

Participants

4

Reactant 2

HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 72305307HCID 72305307, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tetrahydrofuran-3-carboxaldehyde (50% solution in water, 2.5 mL, 12.5 mmol) in ethanol (5.0 mL) is stirred with hydroxylamine-hydrochloride (1.3 g, 18.7 mmol) for 3 h. The reaction is quenched with 0.1 M HCl and extracted with EtOAc, dried over MgSO4, filtered, and concentrated to give the oxime as a colorless oil. A solution of the oxime (115 mg, 1.0 mmol) in DMF (1 mL) is then treated with N-chlorosuccinimide (147 mg, 1.1 mmol) at 40° C. for 2 h. The reaction is then cooled to room temperature, poured on to ice water and extracted with diethyl ether (3×10 mL). The combined organics are dried over MgSO4, filtered, and concentrated to give tetrahydrofuran-3-carbonyl chloride oxime, which is used without further purification.

Workup

  1. customThe reaction is quenched with 0.1 M HCl
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-26453ea6c2124c33afb869cb7f0f5502
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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