Hydrochloric Acid → HCID 19047585, compound

HRID 1780913Notes

Reaction equation

HRID 1780913 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]#[C:7][CH2:8][OH:9])=[CH:2]1.[C:10](OC(=O)C)(=[O:12])[CH3:11].Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:10]([O:9][CH2:8][C:7]#[C:6][C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 227309543-(Furan-3-yl)prop-2-yn-1-ol

Product 1

HCID 19047585HCID 19047585, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(3-furyl)-2-propynyl alcohol (1.45 g, 0.0118 mol), DMAP (1 mg), TEA (2.46 ml, 0.017 mol), and acetic anhydride (1.6 ml, 0.017 mol) in 25 ml of methylene chloride was stirred for 1 hour and the mixture was poured into cold 1 N HCl solution. The mixture was extracted with ether (3×50 ml), the organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (hexane/ether, 2:1) to afford 1.44 g (57.5%) of 3-(3-acetyloxy-1-propynyl)furan as a clear oil.

Workup

  1. extractionThe mixture was extracted with ether (3×50 ml)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica column chromatography (hexane/ether, 2:1)

Sources & evidence

ORD record
ord-fda4a291a31f49d1ad96851e7bc4285b
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

Loading…