تفاعل #960884

معادلة التفاعل

n-butyllithium

6-bromo-2,2-dimethyl-4H-spiro[chromene-3,3′-oxetan]-4-one

→

6-bromo-2,2-dimethyl-4-methylene-4H-spiro[chromene-3,3′-oxetane]

المردود 92.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONTo the mixture was added
2. 2
   workup.STIRRINGThe mixture was stirred for 1 hour at ambient temperature
3. 3
   أخرىThe reaction was quenched
4. 4
   workup.ADDITIONby adding water in an ice-water bath
5. 5
   أخرىThe mixture was partitioned between EtOAc-hexane (1:2) and water
6. 6
   غسيلThe organic layer was washed with brine
7. 7
   تجفيفdried over MgSO4
8. 8
   ترشيحfiltered
9. 9
   أخرىthe filtrate was evaporated
10. 10
    أخرىPurification

الإجراء التجريبي

To a suspension of methyl(triphenyl)phosphonium bromide (8.13 g, 22.3 mmol) in THF (44 mL) was added n-butyllithium (1.65 M in n-hexane, 13.5 mL, 22.3 mmol) in a dry ice-acetone bath under argon atmosphere. The mixture was stirred for 60 minutes in an ice bath. To the mixture was added a mixture of 6-bromo-2,2-dimethyl-4H-spiro[chromene-3,3′-oxetan]-4-one (2.21 g, 7.44 mmol) and THF (11 mL) in an ice bath. The mixture was stirred for 1 hour at ambient temperature. The reaction was quenched by adding water in an ice-water bath. The mixture was partitioned between EtOAc-hexane (1:2) and water. The organic layer was washed with brine, dried over MgSO4, filtered, and the filtrate was evaporated. Purification using silica gel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 0 to 20%) afforded 6-bromo-2,2-dimethyl-4-methylene-4H-spiro[chromene-3,3′-oxetane] (2.02 g).

المصدر