Formaldehyde → 6-(5-Methyl-2-phenyl-oxazol-4-yl)-hex-2-yn-1-ol

HRID 2121698Notes

Reaction equation

HRID 2121698 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH2:15][C:16]#[CH:17].[Li]CCCC.[CH2:23]=[O:24]>C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH2:23][OH:24]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 120932685-Methyl-4-pent-4-ynyl-2-phenyl-oxazoleHCID 178418339Butyllithium

Product 1

HCID 120932696-(5-Methyl-2-phenyl-oxazol-4-yl)-hex-2-yn-1-olYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Alkyne 1-7 (1.44 g, 6.4 mmol) was dissolved in THF (100 mL) at −78° C. under N2 atmosphere. nBuLi (5.6 mL, 9.0 mmol) was then added and the reaction stirred at −78° C. for 1 hour. Paraformaldehyde (320 mg, 9.6 mmol) was then added in one portion and the reaction stirred while allowing equilibration to 23° C. over 16 hours. Reaction was washed with dilute aqueous HCl, water, brine, and dried over MgSO4. After removing solvent in vacuo chromatography of the residue with 25% EtOAc/Hexanes gave 1.5 g of the product 1-8 as a clear yellowish oil (92%). NMR CDCl3 (δ): 7.97 (@H, m); 7.43 (3H, m); 4.25 (2H, t, J=2.2, 4.4 Hz); 2.60 (2H, t, J=7.3, 14.6 Hz); 2.33 (3H, s); 2.27 (2H, m); 1.89 (2H, m). M+1=256.2.

Workup

  1. stirringthe reaction stirred
  2. customto 23° C.
  3. customover 16 hours
  4. customReaction
  5. washwas washed with dilute aqueous HCl, water, brine
  6. dry with materialdried over MgSO4
  7. customAfter removing solvent in vacuo chromatography of the residue with 25% EtOAc/Hexanes

Sources & evidence

ORD record
ord-5744a3986f024e77accf97ba77ba5794
Source dataset
uspto-grants-2004_02
Patent number
US06696474B2

Reaction notes

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