تفاعل #1949667

ord-4c5a9dec58c944f295f5f395135e6f11

معادلة التفاعل

C[N+]1([O-])CCOCC1
4-methylmorpholine N-oxide
CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@@H](O)C1
(1S, 4R)-4-(tert-butyldimethylsilanyloxy)cyclopent-2-enol
CC(C)(C)[Si](C)(C)O[C@H]1C=CC(=O)C1
above titled compound
المردود 86.0%
CC(C)(C)[Si](C)(C)O[C@H]1C=CC(=O)C1
(R)-4-(tert-Butyldimethylsilanyloxy)cyclopent-2-enone
المردود 86.0%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىprepared
  2. 2
    تركيزThe filtrate was concentrated in vacuo

الإجراء التجريبي

Tetrapropylammonium perruthenate (9.4 mg, 0.027 mmol) was added to a mixture of (1S, 4R)-4-(tert-butyldimethylsilanyloxy)cyclopent-2-enol prepared, according to Tetrahedron Letters, Vol. 37, No. 18, 1996, pp. 3083-6, (118.6 mg, 0.54 mmol), 4-methylmorpholine N-oxide (94.9 mg, 0.81 mmol) and crushed 4 Å sieves (270 mg) in CH2Cl2 (10 mL). The mixture was stirred for 30 min and was passed through a plug of silica gel with CH2Cl2. The filtrate was concentrated in vacuo to give 100 mg (86%) of the above titled compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06538018B1uspto-grants-2003_03