Tetrahydrofuran → HCID 21934776, compound

HRID 1241468Notes

Reaction equation

HRID 1241468 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17]1[CH2:21]OC[CH2:18]1>>[CH2:21]([O:10][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])[CH:17]=[CH2:18]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 5201014-Chloro-2-hydroxybenzaldehyde

Product 1

HCID 21934776HCID 21934776, compoundYield 97%

Procedure

A mixture of 4-chloro-2-hydroxybenzaldehyde (254 mg, 1.62 mmol) and cesium carbonate (793 mg, 2.43 mmol) in THF (3 mL) was heated to reflux for 3 h. After the reaction mixture was cooled at room temperature, the solvent was evaporated and the residue partitioned between ethyl acetate and hydrochloric acid (1N). The organic layer was collected, dried with sodium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (AcOEt/Hexanes, 1:9) to give the title product (97%): 1H NMR (400 MHz, Cl3CD) δ 10.46 (s, 1H), 7.80 (d, J=8.3 Hz, 1H), 7.05 (dd, J=0.78, 8.3 Hz, 1H), 6.99 (d, J=0.78 Hz, 1H), 6.09 (m, 1H), 5.45 (m, 2H), 4.67 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customthe solvent was evaporated
  4. customthe residue partitioned between ethyl acetate and hydrochloric acid (1N)
  5. customThe organic layer was collected
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by column chromatography (AcOEt/Hexanes, 1:9)

Sources & evidence

ORD record
ord-4990d46c50594b299449ae901c58eebb
Source dataset
uspto-grants-2006_10
Patent number
US07115598B2

Reaction notes

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