3-(p-Tolyl)propiolaldehyde → 1-p-Tolyl-hex-5-en-1-yn-3-ol

HRID 1096697ノート

反応式

HRID 1096697 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([C:7]#[C:8][CH:9]=[O:10])=[CH:3][CH:2]=1.[CH2:12]([Mg]Br)[CH:13]=[CH2:14]>C1COCC1>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([C:7]#[C:8][CH:9]([OH:10])[CH2:14][CH:13]=[CH2:12])=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 113848723-(p-Tolyl)propiolaldehydeHCID 178455850HCID 178455850、化合物

生成物 1

HCID 597791321-p-Tolyl-hex-5-en-1-yn-3-ol収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-p-tolylprop-2-yn-1-al (4.69 g; 32.5 mmol; 1 eq) in THF (40 mL) was added to a solution of allylmagnesium bromide (49 mL; 1M in Et20, 1.5 eq) at 0° C. over 25 minutes. Stirring was continued for an additional 2 h, and the reaction was carefully quenched with water (50 mL) at 0° C. MTBE (100 mL) was added, the layers were stirred, and then allowed to separate. The aqueous phase was re-extracted with MTBE (50 mL) and the combined organic layers were dried over sodium sulfate and filtered. The filtrate was concentrated using a rotary evaporator, and purification of the residue by flash chromatography (4:1→2:1 heptane/EtOAc) afforded the desired homoallylic alcohol (4.9 g; 26.3 mmol; 81%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.34 ((s, 3 H)) 2.56 (t, 2 H) 4.64 (t, 1H) 5.19-5.26 (m, 2H) 5.88-5.99 (m, 1H) 7.10 (d, 2H) 7.31 (d, 2H).

後処理

  1. customthe reaction was carefully quenched with water (50 mL) at 0° C
  2. additionMTBE (100 mL) was added
  3. stirringthe layers were stirred
  4. customto separate
  5. extractionThe aqueous phase was re-extracted with MTBE (50 mL)
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customa rotary evaporator, and purification of the residue by flash chromatography (4:1→2:1 heptane/EtOAc)

出典と根拠

ORDレコード
ord-6e49c683611740829563970e3c2d0f74
出典データセット
uspto-grants-2012_03
特許番号
US08138377B2

反応ノート

読み込み中…