[ CAS No. 1394119-83-5 ]

Name: 1394119-83-5|3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]cyclobutanemethanol|98%
Brand: Ambeed
SKU: A215380
Rating: 93 (25 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 1394119-83-5 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 1394119-83-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1394119-83-5 ]

SDS Specification

Alternatived Products of [ 1394119-83-5 ]

Product Details of [ 1394119-83-5 ]

CAS No. :	1394119-83-5	MDL No. :	MFCD23106334
Formula :	C₁₁H₂₄O₂Si	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QNUGWZOQASOOEE-UHFFFAOYSA-N
M.W :	216.39	Pubchem ID :	66698189
Synonyms :

Safety of [ 1394119-83-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1394119-83-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1394119-83-5 ]
Downstream synthetic route of [ 1394119-83-5 ]

[ 1394119-83-5 ] Synthesis Path-Upstream 1~3

1
[ 18162-48-6 ]
[ 1394119-83-5 ]
[ 1245647-19-1 ]

Reference： [1] Patent: US2012/214762, 2012, A1, . Location in patent: Page/Page column 97

2
[ 23761-23-1 ]
[ 1394119-83-5 ]
[ 1245647-19-1 ]

Reference： [1] Patent: US2012/214762, 2012, A1,

3
[ 17205-02-6 ]
[ 1394119-83-5 ]

Reference： [1] Patent: EP3418282, 2018, A1,

[ 1394119-83-5 ] Synthesis Path-Downstream 1~14

1
[ 18162-48-6 ]
3-(hydroxymethyl)cyclobutanol [ No CAS ]
[ 1394119-83-5 ]
[ 1245647-19-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃;	Step 2-Synthesis of 3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclobutanol (36-b1) and [3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-methanol (36-b2) To a solution of 3-hydroxymethyl-cyclobutanol (0.4 g, 4 mmol) in DCM (20 mL) was added triethylamine (1.2 g, 12 mmol) and tert-butyl-chloro-dimethyl-silane (1.2 g, 8 mmol). The solution was stirred overnight at room temperature. The reaction mixture was then washed with water (*3) and the organic layers concentrated in vacuo. The crude residue was purified by flash chromatography to afford a mixture of 3-(tert-butyl-dimethyl-silanyloxymethyl)cyclobutanol and [3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-methanol (0.6 g, 69%).

Reference： [1]Patent: US2012/214762,2012,A1 .Location in patent: Page/Page column 97

2
[ 1394119-83-5 ]
[ 1245647-19-1 ]
[ 939775-62-9 ]
[ 1272656-62-8 ]

Yield	Reaction Conditions	Operation in experiment
	With Dess-Martin periodane; In dichloromethane; ethyl acetate; at 20℃; for 3h;	Step 3-Synthesis of 3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclobutanone (36-c1) and 3-(tert-butyl-dimethyl-silanyloxy)-cyclobutanecarbaldehyde (36-c2) To a mixture of 3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclobutanol (36-b1) and <strong>[1394119-83-5][3-(tert-butyl-dimethyl-silanyloxy)-cyclobutyl]-methanol</strong> (36-b2) (0.5 g, 2.31 mmol) in DCM (10 mL) was added Dess-Martin reagent (1.47 g, 3.5 mmol). The reaction mixture was stirred for 3 hr at room temperature and then washed with water. The crude residue was purified by flash chromatography (Isolute column), elution with 5% petroleum ether in EtOAc afforded a mixture of 3-(tert-butyl-dimethyl-silanyloxymethyl)-cyclobutanone (36-c1) and 3-(tert-butyl-dimethyl-silanyloxy)-cyclobutanecarbaldehyde (36-c2), (0.44 g, 89%).

Reference： [1]Patent: US2012/214762,2012,A1 .Location in patent: Page/Page column 97

3
[ 23761-23-1 ]
[ 1394119-83-5 ]
[ 1245647-19-1 ]

Reference： [1]Patent: US2012/214762,2012,A1

4
[ 1394119-83-5 ]
[ 1272656-62-8 ]

Yield	Reaction Conditions	Operation in experiment
58.21%		Oxalyl chloride (915.06 mg, 7.21 mmol, 631.08 muL) was added in a solution of dimethyl sulfoxide (938.76 mg, 12.02 mmol, 938.76 muL) in dichloromethane (30.00 mL). The reaction solution was stirred at -78C for 0.5 h, and then added with <strong>[1394119-83-5]3-[tert-butyl(dimethyl)silyl]oxycyclobutylmethanol</strong> (1.30 g, 6.01 mmol) with further stirring for 0.5 h. Triethylamine (3.04 g, 30.05 mmol, 4.17 mL) was then added thereto, and the reaction solution was stirred at -78C for 0.5 h. After completion of reaction, the system was added with 20 mL of water to quench the reaction, and filtered under suction. The filtrate was extracted with ethyl acetate (20 mL * 3). The organic phase was combined and washed with 30 mL of saturated brine. The obtained organic phase was dried over anhydrous sodium sulfate, filtered under suction and evaporated under reduced pressure. The obtained crude compound was purified by column chromatography to give the compound of 3-[tert-butyl(dimethyl)silyl]oxycyclobutylcarboxaldehyde (750 mg, 3.50 mmol, yield of 58.21%) as a colorless liquid. 1H NMR (400MHz, CHLOROFORM-d) delta = 9.84 - 9.59 (m, 1H), 4.37 - 4.19 (m, 1H), 3.06 - 2.36 (m, 3H), 2.24 - 2.09 (m, 2H), 0.89 - 0.86 (m, 9H), 0.07 - 0.01 (m, 6H).
5.2 g		To a solution of oxalyl chloride (5.8 ml, 66.5 mmol, 1.2 equiv) in DCM (165 mL) at -78 C. was added DMSO (9.4 ml, 133 mmol, 2.4 equiv). After stirred for 10 mins, a solution of <strong>[1394119-83-5](3-((tert-butyldimethylsilyl)oxy)cyclobutyl)methanol</strong> (12 g, 55.5 mmol) in DCM (20 ml) was added and the resulting solution was stirred at -78 C. for 20 mins. TEA (23 mL, 166 mmol, 3.0 equiv) was added and the mixture was stirred at -78 C. for 10 mins then slowly warmed to 0 C. The reaction was quenched by adding sat. aq. NH4Cl solution. The phase were separated and the aqueous layer was extracted with DCM. The combined organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography, EtOAc/heptane 0 to 20%, to afford product 5.2 g (44% yield). 1H NMR: (400 MHz, CDCl3) -0.2 (s, 6H), 0.8 (s, 9H), 1.94-2.27 (m, 2H), 2.48-2.65 (m, 2H), 2.93-3.15 (m, 1H), 4.17-4.50 (m, 1H), 9.8 (s, 1H).

Reference： [1]Patent: EP3418282,2018,A1 .Location in patent: Paragraph 0559-0560
[2]Patent: US2016/166548,2016,A1 .Location in patent: Paragraph 0454-0455

5
[ 1394119-83-5 ]
tert-butyl(3-ethynylcyclobutoxy)dimethylsilane [ No CAS ]

Reference： [1]Patent: US2016/166548,2016,A1

6
methyl 3-((tert-butyldimethylsilyl)oxy)cyclobutane-1-carboxylate [ No CAS ]
[ 1394119-83-5 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;	A solution of LiAiH4 in THF (77 ml, 1.0 M in THF, 1.1 equiv) was added dropwise to a solution of methyl 3-((tert-butyldimethylsilyl)oxy)cyclobutane-1-carboxylate (17 g, 69.6 mmol) in THF (139 ml) at 0 C. and the resulting solution was stirred at rt for 2 hours. The reaction mixture was then cooled in ice-water bath and quenched by adding sat. aq. Na2SO4 solution (10 ml). After stirred at rt for 30 mins, the mixture was filtered and the filtrate was concentrated. The residue was dissolved in EtOAc and dried over MgSO4 and concentrated. The crude material was continued to the next step with no further purification.

Reference： [1]Patent: US2016/166548,2016,A1 .Location in patent: Paragraph 0453

7
3-carbonylcyclobutylcarboxylic acid [ No CAS ]
[ 1394119-83-5 ]