تفاعل #680576

معادلة التفاعل

lactol

(3aR,6aS)-2-Hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

4-Methylmorpholine N-oxide

→

lactone

المردود 70.0%

(3aR,6aS)-2-Oxo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde

المردود 70.0%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe reaction mixture was stirred at r.t. for 10 min
2. 2
   workup.STIRRINGthe reaction was stirred at r.t. for 14 hours
3. 3
   ترشيحThe reaction mixture was filtered over Celite®
4. 4
   غسيلthe solids were washed with CH2Cl2 (3×10 ml)
5. 5
   تركيزThe organic phase was concentrated
6. 6
   أخرىto give the crude material as a black oil
7. 7
   أخرىThe material was purified by column chromatography
8. 8
   غسيلeluting with CH2Cl2/EtOAc (9:1)

الإجراء التجريبي

Purified lactol 7 (800 mg, 4.15 mmol), was dissolved in CH2Cl2 (52 ml) and stirred at r.t. 4-Methylmorpholine N-oxide (729 mg, 6.23 mmol) and 4 Å molecular sieve (2.8 g) were added as solids and the reaction mixture was stirred at r.t. for 10 min. Tetrapropylammonium perruthenate (146 mg, 0.415 mmol) was added as a solid and the reaction was stirred at r.t. for 14 hours. The reaction mixture was filtered over Celite® and the solids were washed with CH2Cl2 (3×10 ml). The organic phase was concentrated to give the crude material as a black oil. The material was purified by column chromatography eluting with CH2Cl2/EtOAc (9:1), to give the lactone 54, (439 mg, 70%) as a white solid.

المصدر