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

HRID 2121698노트

반응식

HRID 2121698 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5744a3986f024e77accf97ba77ba5794
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696474B2

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