3-Methylnaphthalene-2-carbaldehyde → (3-Methylnaphthalen-2-yl)methanol

HRID 330259ノート

反応式

HRID 330259 の反応式
[CH3:1][C:2]1[C:3]([CH:12]=[O:13])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:13][CH2:12][C:3]1[C:2]([CH3:1])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

参加物

4

反応物 2

HCID 127878253-Methylnaphthalene-2-carbaldehydeHCID 21226445Aluminium lithium hydride

生成物 1

HCID 14699377(3-Methylnaphthalen-2-yl)methanol収率 72%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 3-methylnaphthalene-2-carboxaldehyde (3.40 g, 20 mmol) in dry THF (200 mL) cooled to 0° C. was added lithium aluminum hydride (LAH, 380 mg, 10 mmol), in portions over 10 minutes. The resulting solution was stirred at 0° C. for 1.5 hours. Excess LAH was quenched by the addition of H2O (50 mL) and the THF was removed in vacuo. The residue was diluted with 1N HCl (150 mL) and extracted with Et2O (3×200 mL). The organics were dried (MgSO4) and concentrated in vacuo to give the crude product as a tan solid. This material was purified by preparative HPLC (SiO2 : 1:1 CH2Cl2 /hexane) to afford the title compound as a white solid (2.47 g, 72%).

後処理

  1. customExcess LAH was quenched by the addition of H2O (50 mL)
  2. customthe THF was removed in vacuo
  3. additionThe residue was diluted with 1N HCl (150 mL)
  4. extractionextracted with Et2O (3×200 mL)
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give the crude product as a tan solid
  8. customThis material was purified by preparative HPLC (SiO2 : 1:1 CH2Cl2 /hexane)

出典と根拠

ORDレコード
ord-915b9ba038104c8bb52b5dd8c4c8e71b
出典データセット
uspto-grants-1990_01
特許番号
US04895861

反応ノート

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