9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol

Base Information

• Chemical Name: 9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol
• CAS No.: 1312466-23-1
• Molecular Formula: C₂₅H₂₄O₆
• Molecular Weight: 420.462
• Mol file: 1312466-23-1.mol

Synonyms:9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol

Chemical Property of 9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol

There total 12 articles about 9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol 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: 89.0%

9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6a-hydroxy-6H-benzofuro[3,2-c]chromen-7-yl 4-methylbenzenesulfonate (1312466-22-0) → 9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol (1312466-23-1)

Guidance literature:

With lithium borohydride; nickel dichloride; In tetrahydrofuran; for 7h; Reflux;

DOI:10.1021/ol201332u

Reference yield:

2-bromo-4-hydroxybenzaldehyde (22532-60-1) → 9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol (1312466-23-1)

Guidance literature:

Multi-step reaction with 9 steps

1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 °C

2: tetrahydrofuran; ethanol / 6 h / 0 °C / Reflux

3: magnesium bromide / diethyl ether / 2 h / 20 °C

4: 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / tetrahydrofuran / 0.5 h / -78 °C

5: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C

6: triethylamine / dichloromethane / 3 h / 20 °C

7: lithium borohydride / tetrahydrofuran / 0 - 20 °C

8: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; caesium carbonate / toluene / 7 h / 90 °C / Inert atmosphere

9: lithium borohydride; nickel dichloride / tetrahydrofuran / 7 h / Reflux

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium borohydride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; caesium carbonate; triethylamine; magnesium bromide; nickel dichloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Darzens condensation / 4: Feist-Benary interrupted synthesis;

DOI:10.1021/ol201332u

Reference yield:

ethyl 3-(4-benzyloxy-2-bromophenyl)-2-ethoxyoxirane-2-carboxylate (1312466-17-3) → 9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol (1312466-23-1)

Guidance literature:

Multi-step reaction with 7 steps

1: magnesium bromide / diethyl ether / 2 h / 20 °C

2: 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / tetrahydrofuran / 0.5 h / -78 °C

3: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C

4: triethylamine / dichloromethane / 3 h / 20 °C

5: lithium borohydride / tetrahydrofuran / 0 - 20 °C

6: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; caesium carbonate / toluene / 7 h / 90 °C / Inert atmosphere

7: lithium borohydride; nickel dichloride / tetrahydrofuran / 7 h / Reflux

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; lithium borohydride; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; caesium carbonate; triethylamine; magnesium bromide; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2: Feist-Benary interrupted synthesis;

DOI:10.1021/ol201332u

upstream raw materials:

ethyl 3-(4-benzyloxy-2-bromophenyl)-2-ethoxyoxirane-2-carboxylate

ethyl 3-bromo-3-(4-benzyloxy-2-bromophenyl)-2-oxopropanoate

C₂₇H₂₇BrO₈

ethyl 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3,4-dihydroxybenzofuran-3-carboxylate

Downstream raw materials:

3-benzyloxy-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a,9-diol