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

HRID 2121698ノート

反応式

HRID 2121698 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5744a3986f024e77accf97ba77ba5794
出典データセット
uspto-grants-2004_02
特許番号
US06696474B2

反応ノート

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