2H-1-Benzopyran-5-ol,2-ethenyl-3,4-dihydro-2,7-dimethyl-,(2R)-(9CI)

Base Information

• Chemical Name: 2H-1-Benzopyran-5-ol,2-ethenyl-3,4-dihydro-2,7-dimethyl-,(2R)-(9CI)
• CAS No.: 783332-65-0
• Molecular Formula: C13H16 O2
• Molecular Weight: 0
• Mol file: 783332-65-0.mol

Synonyms:2H-1-Benzopyran-5-ol,2-ethenyl-3,4-dihydro-2,7-dimethyl-,(2R)-(9CI)

Chemical Property of 2H-1-Benzopyran-5-ol,2-ethenyl-3,4-dihydro-2,7-dimethyl-,(2R)-(9CI)

Chemical Property:

• PSA: 29.46000
• LogP: 2.97030

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2H-1-Benzopyran-5-ol,2-ethenyl-3,4-dihydro-2,7-dimethyl-,(2R)-(9CI)

There total 13 articles about 2H-1-Benzopyran-5-ol,2-ethenyl-3,4-dihydro-2,7-dimethyl-,(2R)-(9CI) 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: 94.0%

(R)-5-methoxy-2,7-dimethyl-2-vinylchroman (593251-70-8) → (R)-2,7-dimethyl-2-vinylchroman-1-ol (783332-65-0)

Guidance literature:

With sodium thioethylate; In N,N-dimethyl-formamide; at 120 ℃; for 24h;

DOI:10.1021/ja048078t

Reference yield:

orcinol (504-15-4) → (R)-2,7-dimethyl-2-vinylchroman-1-ol (783332-65-0)

Guidance literature:

Multi-step reaction with 12 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

With pyridine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; Wilkinson's catalyst; n-butyllithium; 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; triphenylphosphine; zinc(II) chloride; sodium thioethylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; 7.2: Negishi coupling;

DOI:10.1021/ja048078t

Reference yield:

1,3-dimethoxy-5-methylbenzene (4179-19-5) → (R)-2,7-dimethyl-2-vinylchroman-1-ol (783332-65-0)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; Wilkinson's catalyst; n-butyllithium; 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; triphenylphosphine; zinc(II) chloride; sodium thioethylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; N,N-dimethyl-formamide; pentane; 6.2: Negishi coupling;

DOI:10.1021/ja048078t

upstream raw materials:

(R)-5-methoxy-2,7-dimethyl-2-vinylchroman

orcinol

1,3-dimethoxy-5-methylbenzene

2,6-dimethoxy-4-methylbenzaldehyde

Downstream raw materials:

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

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