Реакция #214740

Уравнение реакции

11-t-Butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-6-hydroxy-5-oxo-1-tosyloxyundecane

dimethyl sulfoxide

acetic anhydride

→

11-t-butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-6-methylthiomethoxy-5-oxo-1-tosyloxyundecane

Выход 91.0%

Условия реакции

Обработка

1. 1
   ДругоеThe solvents are removed in vacuo below 70° C.
2. 2
   Другоеthe residue is partitioned between ether and saturated sodium bicarbonate solution
3. 3
   ПромывкаThe organic layer is washed with brine
4. 4
   Сушкаdried (sodium sulfate)
5. 5
   ДругоеThe solvent is removed in vacuo

Методика

11-t-Butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-6-hydroxy-5-oxo-1-tosyloxyundecane (1.15 g) is dissolved in dimethyl sulfoxide (8.15 ml), acetic anhydride (8.15 ml) is added and the resulting solution is stirred for 20 hours. The solvents are removed in vacuo below 70° C. and the residue is partitioned between ether and saturated sodium bicarbonate solution. The organic layer is washed with brine and dried (sodium sulfate). The solvent is removed in vacuo to give 11-t-butyldiphenylsiloxy-6,10-dimethyl-2,2-ethylenedioxy-6-methylthiomethoxy-5-oxo-1-tosyloxyundecane (1.13 g, 91%) as a yellow oil; nmr (CDCl3,δ) 0.88 (d, CH3CH), 1.04 [s, (CH3)3 -C], ##STR29## 2.17 (s, SCH3), 2.42 (s, CH3 -Ph), 3.42 (d, OCH2CH), 3.89 (s, OCH2CH2O and TsOCH2C), 4.41 (s, OCH2S), 7.2-7.9 (aromatic H).

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