2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran

Base Information

• Chemical Name: 2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran
• CAS No.: 144918-23-0
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 144918-23-0.mol

Synonyms:2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran

Chemical Property of 2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran

There total 7 articles about 2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran 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: 100.0%

ethyl rac-(2R,3R)-2-(3,4-dimethoxyphenyl)-4-methylenetetrahydrofuran-3-carboxylate (144918-22-9) → 2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran (144918-23-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 3h; Heating;

DOI:10.1016/S0040-4039(00)61118-8

Reference yield: 78.0%

1-(3,4-dimethoxyphenyl)-1-(prop-2-ynyloxy)-2,3-epoxypropane (203924-98-5) → 2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran (144918-23-0)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1021/jo971526d

Reference yield:

1'-Hydroxymethyleugenol (31706-95-3) → 2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-4-methylenetetrahydrofuran (144918-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / m-chloroperoxybenzoic acid / CHCl₃ / 0 - 20 °C

2.1: sodium hydride / tetrahydrofuran; dimethylsulfoxide / 20 °C

2.2: 82 percent / tetrahydrofuran; dimethylsulfoxide / 4.5 h / 0 - 20 °C

3.1: 78 percent / bis(cyclopentadienyl)titanium(III) chloride / tetrahydrofuran / 1.5 h / 20 °C

With bis(cyclopentadienyl)titanium dichloride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; dimethyl sulfoxide; 1.1: Epoxidation / 2.1: Metallation / 2.2: Etherification / 3.1: Cyclization;

DOI:10.1021/jo971526d

upstream raw materials:

ethyl rac-(2R,3R)-2-(3,4-dimethoxyphenyl)-4-methylenetetrahydrofuran-3-carboxylate

1-(3,4-dimethoxyphenyl)-1-(prop-2-ynyloxy)-2,3-epoxypropane

1'-Hydroxymethyleugenol

1-(3,4-dimethoxyphenyl)-2,3-epoxypropan-1-ol

Downstream raw materials:

(+/-)-Isogmelinol

(4S,5R)-4-(3,4-Dimethoxy-benzyloxymethyl)-5-(3,4-dimethoxy-phenyl)-dihydro-furan-3-one

(2R,3S)-3-(3,4-Dimethoxy-benzyloxymethyl)-2-(3,4-dimethoxy-phenyl)-4-methylene-tetrahydro-furan

Refernces

• 1、 Roy, Subhas Chandra,Adhikari, Sankar. "Stereoselective Total Synthesis of (+/-)-Paulownin and (+/-)-Isogmelinol through Radical Annulation Route". . p. 8415 - 8422. Retrieved 2007/10/02.