تفاعل #358487

معادلة التفاعل

tert-Butylsulphinamide

product

3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-one

ethyl acetate

→

N((9Z)-3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-ylidene)-2-methylpropane-2-sulfinamide

المردود 99.5%

المذيبات

brine

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe resulting solution was heated
2. 2
   درجة الحرارةto reflux for 18 hrs
3. 3
   ترشيحthe mixture filtered through celite
4. 4
   أخرىThe filtrate was partitioned
5. 5
   استخلاصthe aqueous layer was further extracted with ethyl acetate (2×50 ml)
6. 6
   استخلاصThe combined organic extract
7. 7
   غسيلwas washed with brine
8. 8
   تجفيفdried over MgSO4
9. 9
   تركيزconcentrated in vacuo

الإجراء التجريبي

tert-Butylsulphinamide (3.0, 24 mmol) followed by titanium (IV) ethoxide (4.6 ml, 36 mmol) was added to a stirring solution of the product of Step 3 (4.56 g, 11 mmol) in dry THF (10 ml) and the resulting solution was heated to reflux for 18 hrs. The reaction was poured into a stirring solution of brine (200 ml) and then ethyl acetate (100 ml) was added and the mixture filtered through celite. The filtrate was partitioned and the aqueous layer was further extracted with ethyl acetate (2×50 ml). The combined organic extract was washed with brine, dried over MgSO4 and concentrated in vacuo, to afford N((9Z)-3-chloro-4-{(E)-2-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]vinyl}bicyclo[4.2.1]non-3-en-9-ylidene)-2-methylpropane-2-sulfinamide (5.19 g, 99%). m/z (ES+) 474 (MH)+. Compound taken directly onto next Step.

المصدر