1-Naphthaldehyde → 1-(1-Naphthyl)-1-propanol

HRID 2293677ノート

反応式

HRID 2293677 の反応式
[CH2:1]([Mg]Br)[CH3:2].[C:5]1([CH:15]=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1>O1CCCC1>[C:5]1([CH:15]([OH:16])[CH2:1][CH3:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

参加物

4

反応物 2

HCID 61951-NaphthaldehydeHCID 178418443HCID 178418443、化合物

生成物 1

HCID 124533351-(1-Naphthyl)-1-propanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a flame-dried flask containing 8.0 mL of dry tetrahydrofuran under an argon atmosphere cooled to -78° C. Is added 4.0 mL (3.0 M) of a solution of ethylmagnesium bromide in tetrahydrofuran. The stirrable mixture is treated with a solution of 1.36 g of commercially available 1-naphthaldehyde in 4.0 mL of tetrahydrofuran with a 2 mL rinse. The reaction is stirred at -78° C. for 5 minutes then warmed to room temperature. After 1 hour the mixture is re-cooled to 0° C., carefully quenched with saturated ammonium chloride, and diluted with diethyl ether. The layers are separated; organic phase washed with brine, dried (magnesium sulfate), and concentrated under reduced pressure. The residue is flash column chromatographed using 25% ethyl acetate in hexane to give 1.76 g of the title product as a pale pink oil.

後処理

  1. washrinse
  2. temperaturethen warmed to room temperature
  3. temperatureAfter 1 hour the mixture is re-cooled to 0° C.
  4. customcarefully quenched with saturated ammonium chloride
  5. additiondiluted with diethyl ether
  6. customThe layers are separated
  7. washorganic phase washed with brine
  8. dry with materialdried (magnesium sulfate)
  9. concentrationconcentrated under reduced pressure
  10. customchromatographed

出典と根拠

ORDレコード
ord-a3bae3ce05c84673a4f3379e3f30c941
出典データセット
uspto-grants-1997_11
特許番号
US05686486

反応ノート

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