Tetrahydrofuran → HCID 22009880, compound

HRID 322474Notes

Reaction equation

HRID 322474 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:28]=[CH:27][C:12]([O:13][CH2:14][C:15]3[N:16]=[C:17](/[CH:20]=[CH:21]/[C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[O:18][CH:19]=3)=[CH:11][CH:10]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.O1CCCC1>CO>[N:1]1([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][C:15]3[N:16]=[C:17]([CH2:20][CH2:21][C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[O:18][CH:19]=3)=[CH:27][CH:28]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 22009878HCID 22009878, compound

Product 1

HCID 22009880HCID 22009880, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-(2-thienyl)ethenyl]oxazole (200 mg) in methanol (10 ml)-tetrahydrofuran (4 ml) was hydrogenated on palladium carbon (10%, wet, 70 mg) at 4 atm. After removal of the catalyst by filtration, the filtrate was concentrated. The hydrogenation was repeated three times to obtain 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[2-(2-thienyl)ethyl]oxazole. Recrystallization from ethyl acetate-methanol gave colorless prisms (155 mg, 79%), mp 68-70° C.

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0a323e821b0a4864840cedd65d23ac41
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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