103202-63-7|trans-4-((tert-Butyldimethylsilyl)oxy)cyclohexan-1-ol| Ambeed

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CAS No. :	103202-63-7
Formula :	C₁₂H₂₆O₂Si
M.W :	230.42
SMILES Code :	O[C@H]1CC[C@H](O[Si](C)(C(C)(C)C)C)CC1
MDL No. :	MFCD30802989

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Yield	Reaction Conditions	Operation in experiment
80%	With 1H-imidazole; In N,N-dimethyl-formamide; at 20℃; for 3h;	To a solution of (1 r,4r)-cyclohexane-1 ,4-diol (3 g, 25.8 mmol) and (0875) imidazole(2.64 g, 38.7 mmol) in DMF (30 mL) was added TBS-CI (4.28 g, 28.4 mmol) The mixture was stirred at rt for 3 day. The mixture was diluted with water (150 mL), extracted with DCM three times. The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuum (high vacuum at 70C to remove most DMF ) to afford a light oil. The residue was loaded purified by CombiFlash, eluted with methanol in DCM (0-5%, 30 min). Collected the desired fraction and concentrated in vacuum to afford the title compound (6 g, 80%) as colorless syrup. 1 H NMR (400 MHz, DMSO-d6) delta 3.72 - 3.35 (m, 2H), 1 .80 - 1 .58 (m, 4H), 1 .37 - 1 .06 (m, 4H), 0.82 (s, 9H), 0.00 (s, 6H).
65%	With 1H-imidazole; In N,N-dimethyl-formamide; at 0℃; for 1h;	EXAMPLE 94a Preparation of intermediate trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol To a solution of <strong>[6995-79-5]trans-1,4-cyclohexanediol</strong> (3 g, 26 mmol) in anhydrous N,N-dimethylformamide (30 mL) at 0 C. was added imidazole (1.7 g, 26 mmol) and tert-butyldimethylchlorosilane (3.87 g, 26 mmol). The reaction mixture was then stirred at 0 C. for 1 h. The mixture was partitioned between ethyl acetate and water. Organic layer was separated, aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1;2) to give trans-4-(tert-buyl-dimethyl-silanyloxy)-cyclohexanol as a white solid (3.9 g, 65%). The starting material <strong>[6995-79-5]trans-1,4-cyclohexanediol</strong> was prepared by crystallization from 1:1 mixture of cis-/<strong>[6995-79-5]trans-1,4-cyclohexanediol</strong> according to procedures described by Doyle, M. P. et al in Org. Lett. 2005, Vol 7, No. 22, 5035-5038 supplimental materials without modification.
41%	With 1H-imidazole; In dichloromethane; at 20℃; for 24h;	To a solution of (l,4-/rax)-cyclohexane-l,4-diol (70 g, 602.6 mmol) and imidazole (130 g, 1.910 mol) in dichloromethane (1.5 L) was added /er/-butyl-chloro-dimethyl- silane (100 g, 663.5 mmol) in one portion. The resultant reaction mixture was allowed to warm to room temperature and stir for 24 h, at which time TLC-analysis revealed mixture of starting material, desired product, and bis-addition product. The reaction mixture was poured into water (300 mL). The organic layer was separated, and the aqueous layer was extracted with dichloromethane (100 mL). The combined organic extracts were washed with water (100 mL) and brine (100 mL), dried (0779) (Na2S04), filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (800 g silica gel column, linear gradient of 0- 50percent ethyl acetate in heptane) to afford ( 1 ,4-/ra//.s)-4-[tert- butyl(dimethyl)silyl]oxycyclohexanol (58 g, 41percent) as a white solid. 1H NMR (400 MHz, DMSO-i) d 4.44 (d, J = 4.1 Hz, 1H), 3.69 - 3.50 (m, 1H), 3.48 - 3.35 (m, 1H), 1.84 - 1.60 (m, 4H), 1.37 - 1.09 (m, 4H), 0.84 (s, 9H), 0.02 (s, 6H).

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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CAS No.: 103202-63-7

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CAS No.: 103202-63-7

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[ 103202-63-7 ] Synthesis Path-Downstream 1~1

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed