4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one

Base Information

• Chemical Name: 4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one
• CAS No.: 96845-53-3
• Molecular Formula: C₂₄H₂₆O₄S
• Molecular Weight: 410.534
• Mol file: 96845-53-3.mol

Synonyms:4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one

Chemical Property of 4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one

There total 11 articles about 4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one 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:

5-hydroxymethyl-4,5-dihydrofuranone (10374-51-3) → 4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one (96845-53-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) sodium hydride / 1.) DMF, RT, 1 h, 2.) RT, 2 h

2: 1.) lithium diisopropylamide, 2.) hexamethylphosphoramide / 1.) hexane, tetrahydrofuran, -78 deg C, 1 h, 2.) -78 deg c, 40 min

3: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

4: 81 percent / toluene / 0.5 h / Heating

5: 1.) n-butyllithium, 2.) hexamethylphosphoramide / 1.) tetrahydrofuran, n-hexane, -20 deg C, 1 h, 2.) -78 deg C, 2.5 h

6: 44 percent / Raney nickel / tetrahydrofuran / 4 h / Heating

7: 1.) sodium hydride / 1.) benzene, RT, 30 min, 2.) RT, 1 h

8: 1.) pyridine, methanesulfonyl chloride, 2.) 4-(dimethylamino)pyridine / 1.) RT, 3 h, 2.) RT, 4 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; nickel; sodium hydride; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo00215a034

Reference yield:

(S)-(+)-γ-(methoxymethyl)-γ-butyrolactone (96845-45-3,261911-63-1) → 4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one (96845-53-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) lithium diisopropylamide, 2.) hexamethylphosphoramide / 1.) hexane, tetrahydrofuran, -78 deg C, 1 h, 2.) -78 deg c, 40 min

2: 98 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

3: 81 percent / toluene / 0.5 h / Heating

4: 1.) n-butyllithium, 2.) hexamethylphosphoramide / 1.) tetrahydrofuran, n-hexane, -20 deg C, 1 h, 2.) -78 deg C, 2.5 h

5: 44 percent / Raney nickel / tetrahydrofuran / 4 h / Heating

6: 1.) sodium hydride / 1.) benzene, RT, 30 min, 2.) RT, 1 h

7: 1.) pyridine, methanesulfonyl chloride, 2.) 4-(dimethylamino)pyridine / 1.) RT, 3 h, 2.) RT, 4 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; nickel; sodium hydride; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/jo00215a034

Reference yield:

2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethanol (60100-23-4) → 4β-<2-(1,2-dihydro-4-methoxybenzocyclobutenyl)ethyl>-4,5-dihydro-5α-(methoxymethyl)-3-<(phenylthio)-methylene>furan-2(3H)one (96845-53-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

2: 84 percent / boron trifluoride-diethyl ether / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.) n-butyllithium, 2.) hexamethylphosphoramide / 1.) tetrahydrofuran, n-hexane, -20 deg C, 1 h, 2.) -78 deg C, 2.5 h

4: 44 percent / Raney nickel / tetrahydrofuran / 4 h / Heating

5: 1.) sodium hydride / 1.) benzene, RT, 30 min, 2.) RT, 1 h

6: 1.) pyridine, methanesulfonyl chloride, 2.) 4-(dimethylamino)pyridine / 1.) RT, 3 h, 2.) RT, 4 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; boron trifluoride diethyl etherate; nickel; sodium hydride; methanesulfonyl chloride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00215a034

upstream raw materials:

thiophenol

(S)-3-[1-Hydroxy-meth-(Z)-ylidene]-4-[2-(3-methoxy-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-ethyl]-5-methoxymethyl-dihydro-furan-2-one

5-hydroxymethyl-4,5-dihydrofuranone

(S)-(+)-γ-(methoxymethyl)-γ-butyrolactone