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

Base Information

Chemical Name:6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde
CAS No.:89656-05-3
Molecular Formula:C₂₁H₂₆O₂S
Molecular Weight:342.502
Hs Code.:

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

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

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

There total 18 articles about 6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde 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: 92.0%

: 89656-03-1
6β,8aβ-dimethyl-5-methylene-1-<(phenylthio)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxyaldehyde

: 89656-05-3
6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde

Guidance literature:: With sodium periodate;
DOI:10.1021/jo00185a047

Reference yield:

: 20007-99-2,33878-99-8,100348-93-4,20007-72-1
Wieland-Miescher ketone

: 89656-05-3
6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde

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: NCS, 2percent H₂SO₄ / methanol / 0.5 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; N-chloro-succinimide; borane-THF; ethanol; sulfuric acid; ammonia; dihydrogen peroxide; sodium ethanolate; sodium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; acetic acid; dimethyl sulfoxide; acetone; benzene;
DOI:10.1021/jo00356a002

Reference yield:

: 90878-77-6
5,5-(ethylenedioxy)-4aβ-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalene

: 89656-05-3
6β,8aβ-dimethyl-5-methylene-1-<(phenylsulfinyl)methyl>-trans-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carboxaldehyde

Guidance literature:: Multi-step reaction with 10 steps

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

2: 89.2 percent / NaH / benzene / Ambient temperature

3: K₂CO₃ / acetone / 20 h / Heating

4: NaOEt / ethanol / 7 h / Heating

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

6: 85 percent / 1 N HCl / tetrahydrofuran; acetic acid / Ambient temperature

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

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

10: NCS, 2percent H₂SO₄ / methanol / 0.5 h / 0 °C

With pyridine; hydrogenchloride; sodium hydroxide; N-chloro-succinimide; borane-THF; ethanol; sulfuric acid; dihydrogen peroxide; sodium ethanolate; sodium hydride; potassium carbonate; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; ethanol; acetic acid; dimethyl sulfoxide; acetone; benzene;
DOI:10.1021/jo00356a002