(1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one

Base Information

Chemical Name:(1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one
CAS No.:1369768-84-2
Molecular Formula:C₁₃H₁₃FO₄
Molecular Weight:252.242
Hs Code.:

Synonyms:(1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one

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Chemical Property of (1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one

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Technology Process of (1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one

There total 4 articles about (1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-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:

: 51594-55-9,24969-06-0,13403-37-7
(R)-(-)-epichlorohydrin

: 1369768-83-1
2-[3-fluoro-4-(methoxymethoxy)phenyl]acetonitrile

: 107-30-2
chloromethyl methyl ether

: 1369768-84-2
(1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one

Guidance literature:: 2-[3-fluoro-4-(methoxymethoxy)phenyl]acetonitrile; With sodium hexamethyldisilazane; In tetrahydrofuran; at -15 ℃; for 0.5h;

(R)-(-)-epichlorohydrin; In tetrahydrofuran; at -15 - 35 ℃;

chloromethyl methyl ether;

Reference yield:

: 51594-55-9,24969-06-0,13403-37-7
(R)-(-)-epichlorohydrin

: 1369768-83-1
2-[3-fluoro-4-(methoxymethoxy)phenyl]acetonitrile

: 1369768-84-2
(1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one

Guidance literature:: (R)-(-)-epichlorohydrin; 2-[3-fluoro-4-(methoxymethoxy)phenyl]acetonitrile; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 3h;

With potassium hydroxide; In ethanol; for 8h; Reflux;

With hydrogenchloride; In water; at 0 - 20 ℃; for 3h;
DOI:10.1021/jm400772t

Reference yield:

: 949090-28-2
3-fluoro-4-methoxymethoxybenzaldehyde

: 1369768-84-2
(1S,5R)-1-[3-fluoro-4-(methoxymethoxy)phenyl]-3-oxabicyclo[3.1.0]hexan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 35 °C / Cooling with ice

2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 14 h / 35 °C / Cooling with ice

2.2: 8 h / 80 - 100 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -15 °C

3.2: -15 - 35 °C

With sodium tetrahydroborate; sodium hexamethyldisilazane; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;