Réaction #57024

Équation de réaction

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

LiBH4

→

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

Solvants

THF

MeOH

EtOAc

Conditions de réaction

Traitement

1. 1
   FiltrationThe mixture was filtered through a bed of Celite®
2. 2
   Autrethe filtrate was evaporated under vacuum
3. 3
   TempératureThe mixture was cooled
4. 4
   AutreTHF was removed under vacuum
5. 5
   workup.ADDITIONThe solution was diluted with EtOAc and sat. NH4Cl
6. 6
   AutreThe layers were separated
7. 7
   Séchagethe organic layer was dried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   AutreAfter evaporation

Mode opératoire

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).

Source