Acetic Acid → (4-(5-Chloro-furan-2-ylmethyl)-phenyl)-methanol

HRID 1693911Notes

Reaction equation

HRID 1693911 reaction equation
[Cl:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12]N)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(O)(=[O:18])C.N([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[O:6][C:5]([CH2:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][OH:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 592553974-(5-Chloro-furan-2-ylmethyl)-benzylamine

Product 1

HCID 59255370(4-(5-Chloro-furan-2-ylmethyl)-phenyl)-methanolYield 44%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 4-(5-chloro-furan-2-ylmethyl)-benzylamine (2.6 g) described in Manufacturing Example 62-1-2, acetic acid (25 mL) and water (25 mL) was added sodium nitrite (9.8 g, 140 mmol) at 0° C., which was stirred for 40 minutes at room temperature. Water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. Methanol (25 mL) was added to the residue at 0° C., followed by addition of potassium carbonate (3.3 g, 24 mmol) at the same temperature. This was stirred for 1 hour at the same temperature. Water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride, and the organic layer was concentrated under a reduced pressure. The residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:2) to obtain the title compound (1.2 mg, 44%).

Workup

  1. extractionto extract the reaction mixture
  2. washThe organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. customthe solvent was evaporated under a reduced pressure
  4. additionMethanol (25 mL) was added to the residue at 0° C.
  5. stirringThis was stirred for 1 hour at the same temperature
  6. extractionto extract the reaction mixture
  7. washThe organic layer was washed successively with water, saturated sodium hydrogencarbonate and saturated aqueous sodium chloride
  8. concentrationthe organic layer was concentrated under a reduced pressure
  9. customThe residue was purified by neutral silica gel column chromatography (ethyl acetate:heptane=1:2)

Sources & evidence

ORD record
ord-3fa537307afd40dd94775f22b266c61d
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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