3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran]

Base Information

• Chemical Name: 3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran]
• CAS No.: 139697-95-3
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.242
• Mol file: 139697-95-3.mol

Synonyms:3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran]

Chemical Property of 3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran]

There total 3 articles about 3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran] 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: 82.0%

2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1025707-93-0) + o-bromobenzyl alcohol (18982-54-2) → (2-(3,4-dihydro-2H-pyran-6-yl)phenyl)methanol (304669-40-7) + 3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran] (139697-95-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 100 ℃; for 1h; Microwave irradiation;

DOI:10.1021/ol302088w

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (2-(3,4-dihydro-2H-pyran-6-yl)phenyl)methanol (304669-40-7) + 3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran] (139697-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium tert-butylate; n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Cooling with acetone-dry ice

1.2: 1 h / 0 °C / Cooling with ice

1.3: 20 °C

2.1: sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 1 h / 100 °C / Microwave irradiation

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; potassium tert-butylate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; water; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/ol302088w

Reference yield:

4-(2-(hydroxymethyl)-phenyl)but-3-yn-1-ol (201681-27-8) → (2’R, 6aR,11aR)-4’,5’-dihydro-3’H,5H-spiro[6a,11a-(epoxypropano)indeno[1,2-c]isochromene-11,2’-furan] + 4,5-dihydro-3H,3'H-spiro[furan-2,1'-isobenzofuran] (139697-84-0) + 3′,4′,5′,6′-tetrahydro-spiro[isobenzofuran-1(3H),2′(2H)pyran] (139697-95-3)

Guidance literature:

With 2C₃₂H₁₂BF₂₄^(1-)*C₃₃H₂₆N₈O₅Rh₂⁽²⁺⁾; at 100 ℃; Reagent/catalyst; Time; Catalytic behavior;

DOI:10.1021/om4005059

upstream raw materials:

2-(3,4-dihydro-2H-pyran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

o-bromobenzyl alcohol

3,4-dihydro-2H-pyran

4-(2-(hydroxymethyl)-phenyl)but-3-yn-1-ol