7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan

Base Information

• Chemical Name: 7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan
• CAS No.: 89708-58-7
• Molecular Formula: C₂₁H₂₄OS
• Molecular Weight: 324.487
• Mol file: 89708-58-7.mol

Synonyms:7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan

Chemical Property of 7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan

There total 23 articles about 7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan 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: 61.0%

acetic anhydride (108-24-7) + 6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde (89656-05-3) → 7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan (89708-58-7)

Guidance literature:

at 110 ℃; for 1.5h;

DOI:10.1021/jo00185a047

Reference yield: 43.9%

6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde (89656-03-1) → 7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan (89708-58-7)

Guidance literature:

With N-chloro-succinimide; In tetrachloromethane; for 32h; Heating;

DOI:10.1021/jo00356a002

Reference yield:

Wieland-Miescher ketone (20007-99-2,33878-99-8,100348-93-4,20007-72-1) → 7β,9aβ-dimethyl-6-methylene-1-(phenylthio)-trans-4,5,5a,6,7,8,9,9a-octahydronaphtho<1,2-c>furan (89708-58-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 99.1 percent / p-toluenesulfonic acid / acetic acid / 5 h / Ambient temperature

2: p-toluenesulfonic acid / benzene / 15 h / Heating

3: 73.8 percent / Na, liquid NH₃ / diethyl ether; 1,2-dimethoxy-ethane / 1 h

4: 1.) BH₃*THF, 2.) 3 N NaOH, 30percent H₂₀₂ / 1.) THF, a) 0 deg C, 3 h, b) RT, overnight, 2.) THF, 4 h

5: 89.2 percent / NaH / benzene / Ambient temperature

6: K₂CO₃ / acetone / 20 h / Heating

7: NaOEt / ethanol / 7 h / Heating

8: dimethylsulfoxide / 15 h / 55 - 60 °C

9: 85 percent / 1 N HCl / tetrahydrofuran; acetic acid / Ambient temperature

10: 1.) NaH, 2.) EtOH / 1.) 0 deg C, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, overnight

11: 1.) pyridine, p-toluenesulfonyl chloride / 1.) 1 h, 0 deg C, 2.) a) 0 deg C, 1 h, b) 5 deg C, overnight

13: 43.9 percent / NCS / CCl₄ / 32 h / Heating

With pyridine; hydrogenchloride; sodium hydroxide; N-chloro-succinimide; borane-THF; ethanol; ammonia; dihydrogen peroxide; sodium ethanolate; sodium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; tetrachloromethane; 1,2-dimethoxyethane; diethyl ether; ethanol; acetic acid; dimethyl sulfoxide; acetone; benzene;

DOI:10.1021/jo00356a002

upstream raw materials:

acetic anhydride

6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde

6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde

Wieland-Miescher ketone

Downstream raw materials:

(+/-)-colorata-4(13)8-dienolide