تفاعل #6057

معادلة التفاعل

Methanesulfonyl chloride

2-O-((1,1-dimethylethyl)diphenylsilyl)-3-(((1,1- dimethylethyl)diphenyl-silyl)oxymethyl)-1,2-cyclobutanediol

triethylamine

→

title compound

المردود 60.0%

1-O-methanesulfonyl-2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)di-phenylsilyl)oxymethyl)-1-cyclobutanol

المردود 60.0%

المذيبات

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   غسيلthis solution was washed with 100 mL of water
2. 2
   تجفيفdried over anhydrous magnesium sulfate
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue (2.9 g) was dissolved in 25 mL of 10% acetone in hexane
6. 6
   أخرىpurified on a 2.5×45 cm silica gel column
7. 7
   غسيلeluted at 2 psi with 500 mL of 5% acetone in hexane

الإجراء التجريبي

Freshly distilled triethylamine (1.28 g, 8.2 mmol) was dissolved in 75 mL of freshly distilled methylene chloride. To this solution was added 2.3 g (3.9 mmol) of 2-O-((1,1-dimethylethyl)diphenylsilyl)-3-(((1,1- dimethylethyl)diphenyl-silyl)oxymethyl)-1,2-cyclobutanediol from Step K and the resultant solution was cooled to -78° C. with stirring, under a nitrogen atmosphere. Methanesulfonyl chloride (0.99 g, 8.2 mmol) was added and the reaction mixture was allowed to warm to ambient temperature. After 3.5 h, the reaction mixture was diluted with 125 mL of methylene chloride and this solution was washed with 100 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue (2.9 g) was dissolved in 25 mL of 10% acetone in hexane and purified on a 2.5×45 cm silica gel column eluted at 2 psi with 500 mL of 5% acetone in hexane, followed by 250 mL of 10% acetone in hexane, to give 1.57 g (60% yield) of the title compound; MS DCI-NH3M/Z: 690 (M+NH4)+ ; 1H NMR (CDCl3) δ 1.95, m, 1H), 2.20 (m, 1H), 2.77 (m, 1H), 2.90 (s, 3H), 3.39 (d, 2H), 4.39 (m, 1H), 4.88 (m, 1H), 7.30-7.54 (m, 15H), 7.60-7.70 (m, 5H).

المصدر