반응 #647337

반응 방정식

(4,5-difluoro-indan-1-yl)-acetic acid ethyl ester

LiBH4

→

2-(4,5-difluoro-indan-1-yl)-ethanol

용매

THF

MeOH

EtOAc

반응 조건

후처리

1. 1
   여과The mixture was filtered through a bed of Celite®
2. 2
   기타the filtrate was evaporated under vacuum
3. 3
   온도The mixture was cooled
4. 4
   기타THF was removed under vacuum
5. 5
   workup.ADDITIONThe solution was diluted with EtOAc and sat. NH4Cl
6. 6
   기타The layers were separated
7. 7
   건조the organic layer was dried over MgSO4
8. 8
   여과filtered
9. 9
   기타After evaporation

실험 절차

A mixture of E- and Z-(4,5-difluoro-indan-1-ylidene)-acetic acid ethyl ester (Intermediate TWENTY-3) (1.1 g) in EtOAc (25 mL) was hydrogenated with 10% Pd/C (0.16 g) under H2 (balloon) at rt for 16 h. The mixture was filtered through a bed of Celite® and the filtrate was evaporated under vacuum. The ester, (4,5-difluoro-indan-1-yl)-acetic acid ethyl ester (1.1 g, 4.58 mmol) in THF (60 mL) and MeOH (1 mL) was treated with LiBH4 (0.21 g, 8.5 mmol) at 65° C. for 5 h. The mixture was cooled and THF was removed under vacuum. The solution was diluted with EtOAc and sat. NH4Cl. The layers were separated and the organic layer was dried over MgSO4 and filtered. After evaporation, the alcohol, 2-(4,5-difluoro-indan-1-yl)-ethanol (Intermediate TWENTY-4) was isolated as a clear, colorless oil, 1.7 g, (88%). Use, 2-(4,5-difluoro-indan-1-yl)-ethanol (Intermediate TWENTY-4) in Method SEVENTEEN produced 4-(4,5-difluoro-indan-1-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 156).

출처