(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol

Base Information

Chemical Name:(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol
CAS No.:256440-99-0
Molecular Formula:C₂₆H₃₉ClO₅
Molecular Weight:467.046
Hs Code.:

Synonyms:(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol

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Chemical Property of (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol

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Technology Process of (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol

There total 8 articles about (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol 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: 91.0%

: 256440-98-9
(1R,3R,6R)-1-allyl-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane

: 256440-99-0
(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol

Guidance literature:: (1R,3R,6R)-1-allyl-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane; With Thexylboran; In tetrahydrofuran; at -10 ℃; for 1h;

With sodium hydroxide; water; at 20 ℃; for 5h;
DOI:10.1016/S0040-4020(99)00885-6

Reference yield:

: 5524-05-0
(2R,5R)-5-isopropenyl-2-methylcyclohexanone

: 256440-99-0
(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 55 percent

2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 72 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 83 percent / Et₃N; 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / 50 °C

4.1: 85 percent / diethyl ether / 0.5 h / -78 °C

5.1: 93 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 96 h / 20 °C

6.1: thexylBH₂ / tetrahydrofuran / 1 h / -10 °C

6.2: 91 percent / aq. NaOH; aq. H₂O / 5 h / 20 °C

With dmap; Thexylboran; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Chlorination / 2.1: Metallation / 2.2: Condensation / 3.1: Elimination / 4.1: Grignard reaction / 5.1: Etherification / 6.1: hydroboration / 6.2: Oxidation;
DOI:10.1016/S0040-4020(99)00885-6

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 256440-99-0
(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-(4-methoxyphenylmethoxy)propylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 72 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 83 percent / Et₃N; 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / 50 °C

3.1: 85 percent / diethyl ether / 0.5 h / -78 °C

4.1: 93 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 96 h / 20 °C

5.1: thexylBH₂ / tetrahydrofuran / 1 h / -10 °C

5.2: 91 percent / aq. NaOH; aq. H₂O / 5 h / 20 °C

With dmap; Thexylboran; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Metallation / 1.2: Condensation / 2.1: Elimination / 3.1: Grignard reaction / 4.1: Etherification / 5.1: hydroboration / 5.2: Oxidation;
DOI:10.1016/S0040-4020(99)00885-6