Water → HCID 18359238, compound

HRID 428701Notes

Reaction equation

HRID 428701 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:11])[C:9]#[CH:10])=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(N(CC)CC)C.O>C1COCC1.CN(C=O)C>[C:12]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:11])[C:9]#[CH:10])=[CH:6][CH:7]=1)(=[O:14])[CH3:13]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18359235HCID 18359235, compound

Product 1

HCID 18359238HCID 18359238, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(4-Amino-phenyl)-2-propyn-1-ol (3.0 mmol) (from Step A above) was dissolved in dry THF (20 mL) and DMF (1 mL). Acetic anhydride (4.2 mmol) was added dropwise followed by triethylamine (3.0 mmol). The reaction was stirred at room temperature for 2 h, after which time water (30 mL) was added, and the THF was evaporated in vacuo. The aqueous layer was extracted with ethyl acetate (3×50 mL), and the combined organic layers were dried over magnesium sulfate and concentrated. The resulting product, 3-(4-acetamidophenyl)-3-hydroxy-1-propyne, was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane.

Workup

  1. customthe THF was evaporated in vacuo
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×50 mL)
  3. dry with materialthe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting product, 3-(4-acetamidophenyl)-3-hydroxy-1-propyne, was purified via flash column chromatography (SiO2, 230-400 mesh) with ethyl acetate/hexane

Sources & evidence

ORD record
ord-a4d49b5e9823496e82eae26c41824824
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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