3-Benzyloxybenzaldehyde → 1-(3-(Benzyloxy)phenyl)but-2-yn-1-ol

HRID 1662567

反応式

HRID 1662567 の反応式
[C:1]([Mg]Br)#[C:2][CH3:3].[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([CH:17]([OH:18])[C:1]#[C:2][CH3:3])[CH:19]=[CH:20][CH:21]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 743423-BenzyloxybenzaldehydeHCID 178419101HCID 178419101、化合物

生成物 1

HCID 577059921-(3-(Benzyloxy)phenyl)but-2-yn-1-ol収率 97.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A 1 L round bottom flask was charged with 1-propynylmagnesium bromide (0.5 M in THF) (available from Aldrich) (245 mL, 123 mmol) and cooled to −78° C. To the cold slurry was added a solution of 3-benzyloxybenzaldehyde (available from Aldrich) (20.0 g, 94.2 mmol) in THF (30 mL) over 15 minutes. The mixture was stirred for 30 minutes at −78° C., the cooling bath was removed, and stirring was continued for 1 hour at ambient temperature. The reaction was quenched with saturated aqueous ammonium chloride and diluted with EtOAc. The organics were washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-30% EtOAc/hexane) to afford 93.A (23.1 g, 97% yield) as a pale yellow oil.

後処理

  1. customthe cooling bath was removed
  2. stirringstirring
  3. waitwas continued for 1 hour at ambient temperature
  4. customThe reaction was quenched with saturated aqueous ammonium chloride
  5. additiondiluted with EtOAc
  6. washThe organics were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel flash chromatography (0-30% EtOAc/hexane)

出典と根拠

ORDレコード
ord-2f4894906a1b460db637c4867fb09e6e
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

関連ノート

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