ethyl 7-oxo-1,3,4,5,6,7-hexahydronaphthalene-4a(2H)-carboxylate

Base Information

• Chemical Name: ethyl 7-oxo-1,3,4,5,6,7-hexahydronaphthalene-4a(2H)-carboxylate
• CAS No.: 7478-39-9
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.284
• Mol file: 7478-39-9.mol

Synonyms:

Chemical Property of ethyl 7-oxo-1,3,4,5,6,7-hexahydronaphthalene-4a(2H)-carboxylate

Chemical Property:

• Vapor Pressure: 9.17E-05mmHg at 25°C
• Boiling Point: 339.5°C at 760 mmHg
• Flash Point: 148.8°C
• Density: 1.11g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 7-oxo-1,3,4,5,6,7-hexahydronaphthalene-4a(2H)-carboxylate

There total 1 articles about ethyl 7-oxo-1,3,4,5,6,7-hexahydronaphthalene-4a(2H)-carboxylate 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: 11.0%

ethyl 4-(2',2'-dimethyl-1'-oxopropyloxy)-1-(3'-iodopropyl)-2-methylenecyclohex-3-ene-1-carboxylate (91358-66-6) → ethyl bicyclo[4.4.0]dec-1-en-3-one-6-carboxylate (7478-39-9) + ethyl 2-methyl-4-oxo-1-(prop-2'-enyl)cyclohex-2-ene-1-carboxylate (78872-02-3)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; for 24h; Ambient temperature;

DOI:10.1071/CH9871331

Reference yield:

ethyl bicyclo[4.4.0]dec-1-en-3-one-6-carboxylate (7478-39-9) → (3S,3aS,6aR,10aR)-3-Benzyloxy-5-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-3-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / H₂ / PtO₂ / ethyl acetate / 4 h / Ambient temperature

2: 1.) Br₂, 2.) collidine / 1.) ether, 0 deg C, 7 min., 2.) 170-180 deg C, 45 min.

3: 83 percent / LiAlH₄ / diethyl ether / 24 h / Ambient temperature

4: 80 percent / BaMnO₄-basic, Al₂O₃, CuSO₄*5H₂O / benzene / 5 h / Ambient temperature

5: 84 percent / toluene-p-sulfonyl chloride, pyridine / CH₂Cl₂ / 0.33 h / Ambient temperature

6: 87 percent / t-BuOK / 2-methyl-propan-2-ol / 5 h / Ambient temperature

7: t-BuOK, 2-(4-methoxybenzenesulfonyl)-3-(4-nitrophenyl)oxaziridine / 1 h / Ambient temperature

8: 73 percent / Ag₂O / dimethylformamide / 3 h / Ambient temperature

With pyridine; 2,3,5-trimethyl-pyridine; aluminum oxide; lithium aluminium tetrahydride; barium manganate; 2-(4-methoxybenzenesulfonyl)-3-(4-nitrophenyl)oxaziridine (one equivalent); potassium tert-butylate; hydrogen; bromine; copper(II) sulfate; p-toluenesulfonyl chloride; silver(l) oxide; platinum(IV) oxide; In diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;

DOI:10.1039/p19960001523

Reference yield:

ethyl bicyclo[4.4.0]dec-1-en-3-one-6-carboxylate (7478-39-9) → (3S,3aS,4R,6aR,10aR)-3-Benzyloxy-4-methyl-5-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-3-carboxylic acid methyl ester

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / H₂ / PtO₂ / ethyl acetate / 4 h / Ambient temperature

2: 1.) Br₂, 2.) collidine / 1.) ether, 0 deg C, 7 min., 2.) 170-180 deg C, 45 min.

3: 83 percent / LiAlH₄ / diethyl ether / 24 h / Ambient temperature

4: 80 percent / BaMnO₄-basic, Al₂O₃, CuSO₄*5H₂O / benzene / 5 h / Ambient temperature

5: 84 percent / toluene-p-sulfonyl chloride, pyridine / CH₂Cl₂ / 0.33 h / Ambient temperature

6: 87 percent / t-BuOK / 2-methyl-propan-2-ol / 5 h / Ambient temperature

7: t-BuOK, 2-(4-methoxybenzenesulfonyl)-3-(4-nitrophenyl)oxaziridine / 1 h / Ambient temperature

8: 73 percent / Ag₂O / dimethylformamide / 3 h / Ambient temperature

9: 95 percent / NEt₃ / acetonitrile / 4 h / Ambient temperature

10: CH₂Cl₂ / 20 h / Ambient temperature

11: silica gel / CH₂Cl₂ / 24 h / Ambient temperature

12: 98 percent / H₂ / 10percent Pd/C / ethanol / 2 h / Ambient temperature

With pyridine; 2,3,5-trimethyl-pyridine; aluminum oxide; lithium aluminium tetrahydride; barium manganate; 2-(4-methoxybenzenesulfonyl)-3-(4-nitrophenyl)oxaziridine (one equivalent); potassium tert-butylate; hydrogen; bromine; silica gel; copper(II) sulfate; triethylamine; p-toluenesulfonyl chloride; silver(l) oxide; platinum(IV) oxide; palladium on activated charcoal; In diethyl ether; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;

DOI:10.1039/p19960001523

upstream raw materials:

ethyl 4-(2',2'-dimethyl-1'-oxopropyloxy)-1-(3'-iodopropyl)-2-methylenecyclohex-3-ene-1-carboxylate

Downstream raw materials:

3,4,5,6,7,8-hexahydro-2(1H)-naphthalenone

(+)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone

(-)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone