Реакция #9372

Уравнение реакции

2-indan-2-yl-ethanol

N-methylmorpholine-N-oxide

indan-2-yl-acetic acid

LiAlH4

→

indan-2-yl-acetaldehyde

Растворители

CH2Cl2

CH3CN

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was reacted for 2 h at rt
2. 2
   Другоеquenched with Rochelle's salt solution
3. 3
   Экстракцияextracted with Et2O (3×)
4. 4
   СушкаThe organic layer was dried over MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under vacuum
7. 7
   ДругоеThe alcohol (1.35 g, 94%) was used in the next step without further purification
8. 8
   workup.ADDITIONThe mixture was poured directly onto a column of silica gel
9. 9
   Промывкаeluted with 10% EtOAc

Методика

Use of indan-2-yl-acetic acid (commercially available from Lancaster) (Intermediate SEVENTEEN-1) (1.58 g, 8.88 mmol) in THF (15 mL) was added dropwise to a solution of LiAlH4 (9 mL, 1M in Et2O) in THF (10 mL) at 0° C. The mixture was reacted for 2 h at rt and quenched with Rochelle's salt solution and extracted with Et2O (3×). The organic layer was dried over MgSO4, filtered and concentrated under vacuum. The alcohol (1.35 g, 94%) was used in the next step without further purification. A solution of 2-indan-2-yl-ethanol (1.35 g, 8.32 mmol) in 18 mL of CH2Cl2 and CH3CN (2 mL) was treated with 4 Å molecular sieves (4.2 g) N-methylmorpholine-N-oxide (1.5 g, 13.5 mmol) and TPAP: tetra-n-propylammonium perruthenate (VII) (commercially available from Aldrich) (0.3 g, 0.85 mmol). The mixture was stirred for 16 h at rt. The mixture was poured directly onto a column of silica gel and eluted with 10% EtOAc:hexane. To give indan-2-yl-acetaldehyde (Intermediate SEVENTEEN-2), 1.25 g (˜90%). Indan-2-yl-acetaldehyde (Intermediate SEVENTEEN-2) in Method A produced 4-indan-2-ylmethyl-1,3-dihydro-imidazole-2-thione (Compound 142).

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