(2S,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

Base Information

• Chemical Name: (2S,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one
• CAS No.: 69477-91-4
• Molecular Formula: C₁₇H₂₀O₃S
• Molecular Weight: 304.41
• Mol file: 69477-91-4.mol

Synonyms:

Chemical Property of (2S,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

There total 12 articles about (2S,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-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:

(phenylthio)acetic acid (103-04-8) → (2R,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one (69477-91-4,69477-92-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) BuLi, propyl nitrate, 2) aqueous HCl / in THF/hexane, 1) 0 deg C, 45 min., 2) o deg C, 2h, 3) RT, 2h

2: 1) KOH, 2) HOAc / methanol, 1) 1h -10 deg C, 7h 0 deg C, 2) RT, 2h

3: 80 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 1) -78 deg C, 5 min., 2) 0 deg C, 3h

4: 15 percent / KF / xylene / 1) 30 min., RT, 2) 110 deg C, 4h, 80 deg C, 13h

5: NaIO₄ / methanol / 24 h / Ambient temperature

With hydrogenchloride; potassium fluoride; potassium hydroxide; sodium periodate; n-butyllithium; propyl nitrate; acetic acid; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane; xylene;

DOI:10.1021/jo01303a005

Reference yield:

(phenylthio)acetic acid (103-04-8) → (2S,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one (69477-91-4,69477-92-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) BuLi, propyl nitrate, 2) aqueous HCl / in THF/hexane, 1) 0 deg C, 45 min., 2) o deg C, 2h, 3) RT, 2h

2: 1) KOH, 2) HOAc / methanol, 1) 1h -10 deg C, 7h 0 deg C, 2) RT, 2h

3: 80 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 1) -78 deg C, 5 min., 2) 0 deg C, 3h

4: 56 percent / KF / xylene / 1) 30 min., RT, 2) 110 deg C, 4h, 80 deg C, 13h

5: NaIO₄ / methanol / 24 h / Ambient temperature

With hydrogenchloride; potassium fluoride; potassium hydroxide; sodium periodate; n-butyllithium; propyl nitrate; acetic acid; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane; xylene;

DOI:10.1021/jo01303a005

Reference yield:

(phenylthio)nitromethane (60595-16-6) → (2R,3S)-2-Benzenesulfinyl-3,6,6-trimethyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one (69477-91-4,69477-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) KOH, 2) HOAc / methanol, 1) 1h -10 deg C, 7h 0 deg C, 2) RT, 2h

2: 80 percent / triethylamine, methanesulfonyl chloride / CH₂Cl₂ / 1) -78 deg C, 5 min., 2) 0 deg C, 3h

3: 15 percent / KF / xylene / 1) 30 min., RT, 2) 110 deg C, 4h, 80 deg C, 13h

4: NaIO₄ / methanol / 24 h / Ambient temperature

With potassium fluoride; potassium hydroxide; sodium periodate; acetic acid; methanesulfonyl chloride; triethylamine; In methanol; dichloromethane; xylene;

DOI:10.1021/jo01303a005

upstream raw materials:

trans-3,6,6-trimethyl-2-phenylsulfanyl-3,5,6,7-tetrahydro-2H-benzofuran-4-one

(phenylthio)acetic acid

(phenylthio)nitromethane

(Z)-1-nitro-1-(phenylthio)propene