4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde

Base Information

Chemical Name:4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde
CAS No.:89923-27-3
Molecular Formula:C₁₄H₁₅NO₃
Molecular Weight:245.278
Hs Code.:

4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopent<c>isoxazole-4-carboxaldehyde

Synonyms:4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde

Chemical Property:

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Technology Process of 4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde

There total 11 articles about 4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-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: 84.0%

: 89923-26-2
4β,5α-4-(Hydroxymethyl)-5-(phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

: 89923-27-3
4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.) -78 deg C, 2.) room temp.;
DOI:10.1021/jo00187a001

Reference yield:

: 89923-23-9
4β,5α-5-Hydroxy-4-(hydroxymethyl)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole

: 89923-27-3
4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: imidazole / dimethylformamide / 3 h

2: 1.) NaH / 2.) n-Bu₄NI / 1.) THF, 15 h; 2.) 3 h

3: n-Bu₄NF / tetrahydrofuran / 1 h

4: 84 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 2.) room temp.

With 1H-imidazole; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00187a001

Reference yield:

: 89923-24-0
(3aS,4R,5S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3a,4,5,6-tetrahydro-3H-cyclopenta[c]isoxazol-5-ol

: 89923-27-3
4β,5α,5-(Phenylmethoxy)-3,3aβ,5,6-tetrahydro-4H-cyclopentisoxazole-4-carboxaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 2.) n-Bu₄NI / 1.) THF, 15 h; 2.) 3 h

2: n-Bu₄NF / tetrahydrofuran / 1 h

3: 84 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 2.) room temp.

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00187a001