Ammonium formate → 4-(4-Ethyl-1,3-thiazol-2-yl)-2-propylphenol

HRID 603386Notes

Reaction equation

C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[C:18]([CH2:20][CH3:21])[N:19]=2)=[CH:11][C:10]=1[CH2:22][CH2:23][CH3:24])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CCO>[CH2:20]([C:18]1[N:19]=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:22][CH2:23][CH3:24])[CH:11]=2)[S:16][CH:17]=1)[CH3:21]

Participants

Conditions

Temperature: 40 °C

Procedure

Under an atmosphere of argon, palladium on charcoal (0.10 g) was added to a solution of 2-[4-(benzyloxy)-3-propylphenyl]-4-ethyl-1,3-thiazole (0.86 g, 2.53 mmol) (Example 32) and ammonium formate (1.28 g, 20.3 mmol) in EtOH (45 mL). The mixture was stirred at 40° C. for 2 h, and then cooled to rt. The solvent was evaporated and the material was suspended in EtOAc. This suspension was filtered through a small plug of silica gel and then concentrated to give a crude solid. The product was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 7.66 (s, 1H), 7.56 (d, 1H), 6.77-6.66 (m, 2H), 5.70-5.42 (br, 1H), 2.88-2.76 (m, 2H), 2.64-2.55 (m, 2H), 1.72-1.57 (q, 2H), 1.31 (t, 3H), 0.95 (t, 3H).

Workup

temperaturecooled to rt
customThe solvent was evaporated
filtrationThis suspension was filtered through a small plug of silica gel
concentrationconcentrated
customto give a crude solid
customThe product was used in the next step without further purification

Sources & evidence

ORD record: ord-c848a7dce1204d84ad6f0c36112908db
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07906653B2

Reaction notes

Loading…