(R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane

Base Information

• Chemical Name: (R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane
• CAS No.: 783332-69-4
• Molecular Formula: C₃₁H₃₈O₄Si
• Molecular Weight: 502.726

Synonyms:(R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane

Chemical Property of (R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane

There total 17 articles about (R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

(R)-2-(5-methoxymethoxy-2,7-dimethylchroman-2-yl)-ethyl-tert-butyldiphenylsilyl ether (783332-68-3) → (R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane (783332-69-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In benzene; for 2h; Heating;

DOI:10.1021/ja048078t

Reference yield:

orcinol (504-15-4) → (R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane (783332-69-4)

Guidance literature:

Multi-step reaction with 16 steps

1.1: K₂CO₃ / acetone

2.1: tetramethylene diamine; n-butyllithium / diethyl ether / 3 h / Heating

2.2: 97 percent / diethyl ether / 2 h / 20 °C

3.1: sodium bis(trimethylsilyl)amine / tetrahydrofuran / 3 h / 20 °C

3.2: 98 percent / tetrahydrofuran / -78 - 20 °C

4.1: 85 percent / rhodium tris(phenylphosphine) chloride / tetrahydrofuran / 20 - 50 °C

5.1: 100 percent / aq. sodium hydroxide; aq. hydrogen peroxide / tetrahydrofuran / 1.5 h / 50 °C

6.1: 97 percent / triphenylphosphine; imidazole; iodine / tetrahydrofuran / 1 h / 20 °C

7.1: zinc chloride; tert-butyllithium / tetrahydrofuran; pentane / 3.5 h / -78 - 20 °C

7.2: Pd(dppf)Cl₂; n-butyllithium / tetrahydrofuran; pentane; hexane / 20 °C

8.1: 78 mg / TBAF / tetrahydrofuran / 1 h

9.1: 87 percent / n-propyllithium thiolate / hexamethylphosphoric acid triamide / 120 °C

10.1: 100 percent / pyridine / CH₂Cl₂ / 0 °C

11.1: Pd₂dba3*CHCl₃; (R,R)-1,2-di(o-Ph₂PC₆H₄CONH)cyclohexane; acetic acid / CH₂Cl₂ / 1 h / 20 °C

12.1: 94 percent / NaSEt / dimethylformamide / 24 h / 120 °C

13.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 °C

13.2: 95 percent / tetrahydrofuran / 5 h / 20 °C

14.1: BH₃*THF / tetrahydrofuran / 1 h / 20 °C

14.2: 94 percent / aq. sodium hydroxide; aq. hydrogen peroxide / tetrahydrofuran / 1 h / 50 °C

15.1: 82 percent / triethylamine; DMAP / CH₂Cl₂ / 2.5 h / 20 °C

16.1: 80 percent / DDQ / benzene / 2 h / Heating

With pyridine; 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; Wilkinson's catalyst; n-butyllithium; borane-THF; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; lithium n-propylmercaptide; potassium carbonate; acetic acid; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; sodium thioethylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; benzene; 7.2: Negishi coupling;

DOI:10.1021/ja048078t

Reference yield:

1,3-dimethoxy-5-methylbenzene (4179-19-5) → (R)-tert-butyl-2-(5-methoxymethoxy-2,7-dimethyl-2H-chromen-2-yl)diphenylsilane (783332-69-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: tetramethylene diamine; n-butyllithium / diethyl ether / 3 h / Heating

1.2: 97 percent / diethyl ether / 2 h / 20 °C

2.1: sodium bis(trimethylsilyl)amine / tetrahydrofuran / 3 h / 20 °C

2.2: 98 percent / tetrahydrofuran / -78 - 20 °C

3.1: 85 percent / rhodium tris(phenylphosphine) chloride / tetrahydrofuran / 20 - 50 °C

4.1: 100 percent / aq. sodium hydroxide; aq. hydrogen peroxide / tetrahydrofuran / 1.5 h / 50 °C

5.1: 97 percent / triphenylphosphine; imidazole; iodine / tetrahydrofuran / 1 h / 20 °C

6.1: zinc chloride; tert-butyllithium / tetrahydrofuran; pentane / 3.5 h / -78 - 20 °C

6.2: Pd(dppf)Cl₂; n-butyllithium / tetrahydrofuran; pentane; hexane / 20 °C

7.1: 78 mg / TBAF / tetrahydrofuran / 1 h

8.1: 87 percent / n-propyllithium thiolate / hexamethylphosphoric acid triamide / 120 °C

9.1: 100 percent / pyridine / CH₂Cl₂ / 0 °C

10.1: Pd₂dba3*CHCl₃; (R,R)-1,2-di(o-Ph₂PC₆H₄CONH)cyclohexane; acetic acid / CH₂Cl₂ / 1 h / 20 °C

11.1: 94 percent / NaSEt / dimethylformamide / 24 h / 120 °C

12.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 °C

12.2: 95 percent / tetrahydrofuran / 5 h / 20 °C

13.1: BH₃*THF / tetrahydrofuran / 1 h / 20 °C

13.2: 94 percent / aq. sodium hydroxide; aq. hydrogen peroxide / tetrahydrofuran / 1 h / 50 °C

14.1: 82 percent / triethylamine; DMAP / CH₂Cl₂ / 2.5 h / 20 °C

15.1: 80 percent / DDQ / benzene / 2 h / Heating

With pyridine; 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; Wilkinson's catalyst; n-butyllithium; borane-THF; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; lithium n-propylmercaptide; acetic acid; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; sodium thioethylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; benzene; 6.2: Negishi coupling;

DOI:10.1021/ja048078t

upstream raw materials:

(R)-2-(5-methoxymethoxy-2,7-dimethylchroman-2-yl)-ethyl-tert-butyldiphenylsilyl ether

orcinol

1,3-dimethoxy-5-methylbenzene

2,6-dimethoxy-4-methylbenzaldehyde

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