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Chemical Structure| 101166-65-8 Chemical Structure| 101166-65-8

Structure of 101166-65-8

Chemical Structure| 101166-65-8

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Product Details of [ 101166-65-8 ]

CAS No. :101166-65-8
Formula : C8H19IOSi
M.W : 286.23
SMILES Code : C[Si](OCCI)(C(C)(C)C)C
MDL No. :MFCD09909940
InChI Key :CAAUZMMMFDVBFD-UHFFFAOYSA-N
Pubchem ID :11129873

Safety of [ 101166-65-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 101166-65-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 4
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 62.49
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

9.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

3.09
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.96
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.44
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.84
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.51
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.97

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.85
Solubility 0.0409 mg/ml ; 0.000143 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.85
Solubility 0.04 mg/ml ; 0.00014 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.46
Solubility 0.0983 mg/ml ; 0.000344 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.23 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

3.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

4.2

Application In Synthesis of [ 101166-65-8 ]

* 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.

  • Downstream synthetic route of [ 101166-65-8 ]

[ 101166-65-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 75-21-8 ]
  • [ 18162-48-6 ]
  • [ 101166-65-8 ]
  • 3
  • [ 3406-02-8 ]
  • [ 101166-65-8 ]
  • [ 132785-45-6 ]
  • 4
  • [ 101166-65-8 ]
  • [ 105550-54-7 ]
  • tert-Butyl-[3-(4-chloro-phenylsulfanyl)-hexa-3,4-dienyloxy]-dimethyl-silane [ No CAS ]
  • 5
  • [ 101166-65-8 ]
  • [ 101166-64-7 ]
  • [ 101166-66-9 ]
  • 6
  • [ 101166-65-8 ]
  • [ 137627-17-9 ]
  • 1-(tert-Butyl-dimethyl-silanyl)-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-trimethylsilanyloxy-azetidin-2-one [ No CAS ]
  • 7
  • [ 101166-65-8 ]
  • [ 121846-23-9 ]
  • [ 121846-24-0 ]
  • 8
  • [ 101166-65-8 ]
  • [ 144760-70-3 ]
  • 1-<2'-<<(tert-Butyl)dimethylsilyl>oxy>ethyl>-1-azacyclotetradecan-2,14-dion [ No CAS ]
  • 9
  • [ 89031-81-2 ]
  • [ 101166-65-8 ]
YieldReaction ConditionsOperation in experiment
100% With sodium iodide; In acetone; at 120℃; for 4h;Inert atmosphere; Sealed tube; Microwave irradiation; A solution of TBSCl (30.1 g, 200 mmol) in DCM (50 mL) was added dropwise over 15 min to a stirred solution of 2-chloroethanol (16.0 g, 200 mmol), imidazole (20.4 g, 300 mmol) and DMAP (0.244 g, 2.0 mmol) in DCM (200 mL) at 0 °C under an argon atmosphere, and the resulting mixture was warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (200 mL) and the separated aqueous layer was then washed with DCM (2*100 mL). The combined organic extracts were washed with saturated aqueous NH4Cl (100 mL) and brine (100 mL), then dried over MgSO4 and concentrated to leave 2-chloroethoxy tert-butyl dimethylsilane (37.1 g, 95percent) as a colourless oil. A solution of the silyl ether (3.88g, 20.0mmol) and sodium iodide (8.94g, 60 mmol) in acetone (10mL) was sealed in a microwave vial and heated at 120°C for 4h in a microwave reactor. The vial was cooled to room temperature and the reaction mixture was then diluted with diethyl ether (80mL) and filtered through silica. The filtrate was concentrated to leave 2-iodoethoxy tert-butyl dimethylsilane (5.72g, quant.) as a pale yellow oil, which was used without further purification. A solution of methyl acetoacetate (2.55g, 22.0mmol) in 79 THF (10mL) was added over 10 min to a stirred suspension of sodium hydride (0.88g, 22.0 mmol, 60percent) in THF (50mL) at 0°C under argon. The mixture was stirred for 15 min, and then a solution of n-butyl lithium (11.0 mL, 22.0 mmol, 2.0M in hexane) was added dropwise over 10 min and the mixture was stirred at 0°C for 15 min. A solution of the above, crude iodide (ca. 20 mmol) in THF (10 mL) was added dropwise over 10 min, and the resulting yellow mixture was then warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (100 mL) and diethyl ether (100mL), and the separated aqueous layer was then washed with diethyl ether (2×100mL). The combined organic extracts were washed with brine (100 mL), then dried over MgSO4 and concentrated to leave a pale yellow gum. Purification by column chromatography (25:1, petrol/Et2O) gave the keto ester (5.05 g, 77percent) as a pale yellow oil (10percent enol form): deltaH (400 MHz, CDCl3) 3.73 (3H, s, CO2CH3), 3.61 (2H, t, J=6.0, CH2O), 3.46 (2H, s, CH2), 2.62 (2H, t, J=7.1, CH2C(O)), 1.80 (2H, tt, J=6.0, 7.1, CH2), 0.87 (9H, s, SiC(CH3)3), 0.03 (6H, s, SiCH3); deltaC (100 MHz, CDCl3) 202.6 (C=O), 167.6 (CO2CH3), 61.8 (CH2O), 52.2 (CO2CH3), 49.0 (CH2), 39.4 (CH2), 26.5 (CH2), 25.9 (SiC(CH3)3), 18.2 (SiC(CH3)3), ?5.4 (2×SiCH3); HRMS m/z C13H26O4SiNa+ (MNa+) requires 297.1498, found 297.1498.
  • 10
  • [ 101166-65-8 ]
  • [ 105-45-3 ]
  • [ 116585-05-8 ]
YieldReaction ConditionsOperation in experiment
77% A solution of TBSCl (30.1 g, 200 mmol) in DCM (50 mL) was added dropwise over 15 min to a stirred solution of 2-chloroethanol (16.0 g, 200 mmol), imidazole (20.4 g, 300 mmol) and DMAP (0.244 g, 2.0 mmol) in DCM (200 mL) at 0 °C under an argon atmosphere, and the resulting mixture was warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (200 mL) and the separated aqueous layer was then washed with DCM (2*100 mL). The combined organic extracts were washed with saturated aqueous NH4Cl (100 mL) and brine (100 mL), then dried over MgSO4 and concentrated to leave 2-chloroethoxy tert-butyl dimethylsilane (37.1 g, 95percent) as a colourless oil. A solution of the silyl ether (3.88g, 20.0mmol) and sodium iodide (8.94g, 60 mmol) in acetone (10mL) was sealed in a microwave vial and heated at 120°C for 4h in a microwave reactor. The vial was cooled to room temperature and the reaction mixture was then diluted with diethyl ether (80mL) and filtered through silica. The filtrate was concentrated to leave 2-iodoethoxy tert-butyl dimethylsilane (5.72g, quant.) as a pale yellow oil, which was used without further purification. A solution of methyl acetoacetate (2.55g, 22.0mmol) in 79 THF (10mL) was added over 10 min to a stirred suspension of sodium hydride (0.88g, 22.0 mmol, 60percent) in THF (50mL) at 0°C under argon. The mixture was stirred for 15 min, and then a solution of n-butyl lithium (11.0 mL, 22.0 mmol, 2.0M in hexane) was added dropwise over 10 min and the mixture was stirred at 0°C for 15 min. A solution of the above, crude iodide (ca. 20 mmol) in THF (10 mL) was added dropwise over 10 min, and the resulting yellow mixture was then warmed to room temperature where it was stirred for 12 h. The mixture was quenched with saturated aqueous NH4Cl (100 mL) and diethyl ether (100mL), and the separated aqueous layer was then washed with diethyl ether (2×100mL). The combined organic extracts were washed with brine (100 mL), then dried over MgSO4 and concentrated to leave a pale yellow gum. Purification by column chromatography (25:1, petrol/Et2O) gave the keto ester (5.05 g, 77percent) as a pale yellow oil (10percent enol form): deltaH (400 MHz, CDCl3) 3.73 (3H, s, CO2CH3), 3.61 (2H, t, J=6.0, CH2O), 3.46 (2H, s, CH2), 2.62 (2H, t, J=7.1, CH2C(O)), 1.80 (2H, tt, J=6.0, 7.1, CH2), 0.87 (9H, s, SiC(CH3)3), 0.03 (6H, s, SiCH3); deltaC (100 MHz, CDCl3) 202.6 (C=O), 167.6 (CO2CH3), 61.8 (CH2O), 52.2 (CO2CH3), 49.0 (CH2), 39.4 (CH2), 26.5 (CH2), 25.9 (SiC(CH3)3), 18.2 (SiC(CH3)3), ?5.4 (2×SiCH3); HRMS m/z C13H26O4SiNa+ (MNa+) requires 297.1498, found 297.1498.
  • 11
  • [ 101166-65-8 ]
  • [ 693-02-7 ]
  • [ 96475-79-5 ]
  • 12
  • [ 101166-65-8 ]
  • [ 2321-07-5 ]
  • C28H30O6Si [ No CAS ]
  • 13
  • [ 101166-65-8 ]
  • [ 135513-92-7 ]
  • (2R,3R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3-hydroxy-pentanoic acid tert-butyl ester [ No CAS ]
  • (2R,3S)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3-hydroxy-pentanoic acid tert-butyl ester [ No CAS ]
  • 14
  • [ 108-24-7 ]
  • [ 101166-65-8 ]
  • [ 159213-03-3 ]
  • Acetic acid (1S,2S)-2-[((R)-4-acetoxy-2-methyl-butyryl)-methyl-amino]-1-phenyl-propyl ester [ No CAS ]
  • Acetic acid (1S,2S)-2-[((S)-4-acetoxy-2-methyl-butyryl)-methyl-amino]-1-phenyl-propyl ester [ No CAS ]
  • 15
  • [ 101166-65-8 ]
  • [ 14980-86-0 ]
  • [ 173054-08-5 ]
  • 16
  • [ 101166-65-8 ]
  • [ 159213-03-3 ]
  • (R)-4-Hydroxy-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-butyramide [ No CAS ]
  • (S)-4-Hydroxy-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-butyramide [ No CAS ]
  • 17
  • [ 101166-65-8 ]
  • [ 159213-03-3 ]
  • (S)-4-(tert-Butyl-dimethyl-silanyloxy)-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-butyramide [ No CAS ]
  • [ 175979-69-8 ]
  • 18
  • [ 101166-65-8 ]
  • C13H17NO2(2-)*2Li(1+) [ No CAS ]
  • (S)-4-(tert-Butyl-dimethyl-silanyloxy)-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-2,N-dimethyl-butyramide [ No CAS ]
  • [ 175979-69-8 ]
  • 19
  • [ 13464-19-2 ]
  • [ 101166-65-8 ]
  • 1-(t-BuMe2Si)-2-(phenylthio)ethyl ether [ No CAS ]
  • 3-(tert-Butyl-dimethyl-silanyloxy)-thiopropionic acid S-phenyl ester [ No CAS ]
  • 20
  • [ 101166-65-8 ]
  • 4-[(E)-(S)-2-Methoxymethyl-pyrrolidin-1-ylimino]-methyl}-tetrahydro-pyran-2-one [ No CAS ]
  • 3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(E)-(S)-2-methoxymethyl-pyrrolidin-1-ylimino]-methyl}-tetrahydro-pyran-2-one [ No CAS ]
  • 21
  • [ 101166-65-8 ]
  • [ 123-54-6 ]
  • [ 192197-10-7 ]
  • 22
  • [ 101166-65-8 ]
  • [ 227804-94-6 ]
  • [ 227804-99-1 ]
  • (3R,4R)-4-([2S-(methoxymethyl)tetrahydro-1H-1-pyrrolyl]imino}methyl)-3-(2-[1-(tert-butyl)-1,1-dimethylsilyl]oxy}ethyl)tetrahydro-2H-pyran-2-one [ No CAS ]
  • 23
  • [ 609-14-3 ]
  • [ 101166-65-8 ]
  • ethyl 2-methyl-6-tert-butyldimethylsilyloxy-3-oxohexanoate [ No CAS ]
  • 24
  • [ 72203-94-2 ]
  • [ 101166-65-8 ]
  • [ 313334-05-3 ]
  • 25
  • [ 101166-65-8 ]
  • [ 299178-58-8 ]
  • [ 299178-59-9 ]
  • 26
  • [ 101166-65-8 ]
  • C24H32BrMgN [ No CAS ]
  • (E)-2-decyl-2-(2-hydroxyethyl)-1,3-diphenylaziridine [ No CAS ]
  • 27
  • [ 101166-65-8 ]
  • [ 171819-92-4 ]
  • [ 302897-02-5 ]
  • 28
  • [ 101166-65-8 ]
  • [ 72170-90-2 ]
  • [ 319439-87-7 ]
  • 29
  • [ 101166-65-8 ]
  • [ 119487-96-6 ]
  • (2R,3R)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-decyl-1,3-diphenyl-aziridine [ No CAS ]
  • 30
  • [ 101166-65-8 ]
  • [ 78277-21-1 ]
  • [ 327618-58-6 ]
  • 31
  • [ 101166-65-8 ]
  • [ 346691-24-5 ]
  • [ 346690-37-7 ]
  • 32
  • [ 101166-65-8 ]
  • [ 182496-70-4 ]
  • [ 637342-91-7 ]
  • 33
  • [ 75-03-6 ]
  • [ 18162-48-6 ]
  • [ 101166-65-8 ]
  • 34
  • [ 624-76-0 ]
  • [ 18162-48-6 ]
  • [ 101166-65-8 ]
YieldReaction ConditionsOperation in experiment
98% With 1H-imidazole; In dichloromethane; at 30℃; for 17h; (i) Preparation of (2-iodoethoxy)-tert-butyldimethylsilane To a stirred solution of 2-iodoethanol (17.2 g; 100 mmol) and imidazole (8.17 g; 120 mmol) in dichloromethane (100 mL) was added tert-butyldimethylsilyl chloride (15.83 g; 105 mmol) at such a rate that the reaction temperature did not rise above 30° C. Upon complete addition the solution was left stirring for 17 h, then washed with water (2*50 mL) and brine (50 mL) and dried over MgSO4. Evaporation of the solvent afforded the target compound (28.0 g; 97.8 mmol; 98percent) as a colourless liquid. 1H-NMR (400 MHz) (CDCl3): delta=3.83 (t, 2H, J=7.0 Hz), 3.83 (t, 2H, J=7.0 Hz), 3.20 (t, 2H, J=7 Hz), 0.90 (s, 9H), 0.08 (s, 6H) ppm.
90% With 1H-imidazole; In N,N-dimethyl-formamide; at 30 - 40℃; for 4h; Preparation of tert-butyl(2-iodoethoxy)dimethylsilane After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30° C. to 40° C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL). The organic layer was washed again with salt water (30 mL*3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90percent) of a target compound. This compound was used as it was for the next reaction without purification.
90% With 1H-imidazole; In N,N-dimethyl-formamide; at 30 - 40℃; for 4h; Preparation of tert-butyl(2-iodoethoxy)dimethylsilane After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30°C to 40°C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL). The organic layer was washed again with salt water (30 mLx3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90percent) of a target compound. This compound was used as it was for the next reaction without purification.
With 2-(Dimethylamino)pyridine; N-ethyl-N,N-diisopropylamine; In dichloromethane; Step 2 tert-Butyl-(2-iodo-ethoxy)-dimethyl-silane To 2-iodoethanol (20 gm, 116 mmol) suspended in methylene chloride (500 mL) was added dimethylaminopyridine (100 mg) followed by diisopropylethylamine (30 mL, 174 mmol) and tert-butyldimethylsilyl chloride (19 gm, 128 mmol). The reaction was stirred overnight and the solvent was removed in vacuo and the residue was passed through a short column of silica gel and eluted with 95:5 methylene chloride: methanol. The desired fractions were combined and the solvent was removed in vacuo to give the desired product. 1 H NMR (400 MHz, CDCl3) delta 3.84 (dd, 2H); 3.20 (dd, 2H); 0.9 (m, 9H); 0.1 (m, 6H).
With 1H-imidazole; In dichloromethane; at 20℃; for 20h;Cooling with ice; Large scale; Step C (1,1 -dimethylethyl)(2-iodoethoxy)dimethylsilane .OTBDMS Iodoethanol (2.68 kg, 15.4 mol), CH2CI2 (12 L) and imidizaole (1.556 kg, 22.63 mol) were chilled in an ice bath. A solution of t-butyldimethylchlorosilane (2.536 kg, 16.32 mol) in CH2CI2 (2.5 L) was added to the reaction over a 2 h period. The resulting white suspension was allowed to warm to rt over an 18 h. The reaction was worked up by washing with water and brine). The organic layer was dried (MgSC^) and evaporated under reduced pressure to provide the product of Step C as a light yellow oil. FontWeight="Bold" FontSize="10" H NMR (400MHz, CDC13) delta = 3.75 (t, J = 7.0 Hz, 2 H), 3.11 (t, J = 7.0 Hz, 2 H), 0.77 - 0.89 (m, 10 H), 0.00 (s, 6 H).

  • 35
  • [ 30889-20-4 ]
  • [ 101166-65-8 ]
  • 1-[2-(<i>tert</i>-butyl-dimethyl-silanyloxy)-ethyl]-cyclohexa-2,5-dienecarboxylic acid methyl ester [ No CAS ]
 

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