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

HRID 330259노트

반응식

HRID 330259 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 14699377(3-Methylnaphthalen-2-yl)methanol수율 72%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-915b9ba038104c8bb52b5dd8c4c8e71b
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895861

반응 노트

불러오는 중…