ChemicalBook CAS DataBase List (((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)

(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane) synthesis

13synthesis methods

Product Name:(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)
CAS Number:139356-38-0
Molecular formula:C20H41ClO2Si2
Molecular Weight:405.1624

139356-37-9 Synthesis

2-((3R,5R)-3,5-bis(tert-butyldiMethylsilyloxy)cyclohexylidene)ethanol

139356-37-9
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(((1R,3R)-5-(2-chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)) bis(tert-butyldimethylsilane)

139356-38-0
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Yield:139356-38-0 90%

Reaction Conditions:

with pyridine;bis(trichloromethyl) carbonate in Hexachlorobutadiene at 0 - 20;

Steps:

((1R,3R)-5-(2-Chloroethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tert-butyldimethylsilane) (16)

A solution of pyridine (7.35 g, 93 mmol) in hexane (50 mL) was added over 30 min to a cold solution of compound 15 (18 g, 46.5 mmol) and triphosgene (6.88 g, 23.27 mmol) in hexane at 0 °C. After stirring at 0 °C for 30 min, and then warmed to room temperature and stirred for another 30 min. The reaction mixture was washed with aqueous solution of CuSO₄.5H₂O. The aqueous solution was extracted with hexane. The combined organic layer were dried over Na₂SO₄ and concentrated under reduced pressure to afford compound 16 (17 g, 90%), which was used in the next step without any purification. ¹H NMR (400 MHz, CDCl₃) δ H NMR, 5.52-5.48 (t, 1H, J = 16, 8 Hz), 4.12-4.03 (m, 4H), 2.37-2.27 (m, 2H), 2.24-2.14 (m, 1H), 2.10-2.05 (m, 1H), 1.83-1.78 (m, 1H), 1.74-1.70 (m, 1H), 0.89 (s, 18H), 0.06 (s, 12H); LC-MS (ES⁺) m/z 405.4 (M+H).

References:

Samala, Ramakrishna;Sharma, Somesh;Basu, Manas K.;Mukkanti;Porstmann, Frank [Tetrahedron Letters,2016,vol. 57,# 12,p. 1309 - 1312] Location in patent:supporting information

139356-37-9 Synthesis

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