(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

Base Information

Chemical Name:(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal
CAS No.:481656-19-3
Molecular Formula:C₂₂H₃₀O₄
Molecular Weight:358.478
Hs Code.:

Synonyms:(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

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Chemical Property of (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

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Technology Process of (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

There total 1 articles about (1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal 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: 75.0%

: 26742-33-6
(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

: 52289-93-7
o-Methoxybenzyl bromide

: 481656-19-3
(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

Guidance literature:: (4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal; With lithium; In tetrahydrofuran; ammonia; at -78 - -30 ℃; Inert atmosphere; liquid NH₃;

With water; isoprene; In tetrahydrofuran; at -78 - -30 ℃; Inert atmosphere;

o-Methoxybenzyl bromide; In tetrahydrofuran; at -30 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201100173

Reference yield: 89.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 481656-19-3
(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

: 481656-21-7
(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-2-methylene-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one-5-ethyleneacetal

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In benzene; for 2h; Inert atmosphere; Reflux;

(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal; In benzene; for 12h; Inert atmosphere; Reflux;
DOI:10.1002/ejoc.201100173

Reference yield:

: 481656-19-3
(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,4aβ-dimethyl-1,4,4a,7,8,8aα-hexahydronaphthalene-2,5(3H,7H)-dione-5-ethyleneacetal

: 481656-25-1
(1S,4aS,8aR)-1α-(2-methoxybenzyl)-1β,2β,4aβ-trimethyl-1,2,3,4,4a,7,8,8aα-octahydronaphthalene-5(6H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / t-BuOK / benzene / Heating

2: 97 percent / aq. HCl / tetrahydrofuran / 20 °C

3: 80 percent / H₂; Et₃N / 10 percent Pd/C / methanol / 20 °C / 760 Torr

With hydrogenchloride; potassium tert-butylate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; benzene;