5-Hexenal, 3,3-dimethyl-4-(phenylmethoxy)-, (4S)-

Base Information

Chemical Name:5-Hexenal, 3,3-dimethyl-4-(phenylmethoxy)-, (4S)-
CAS No.:570371-49-2
Molecular Formula:C15H20O2
Molecular Weight:232.323
Hs Code.:

Synonyms:

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Chemical Property of 5-Hexenal, 3,3-dimethyl-4-(phenylmethoxy)-, (4S)-

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Technology Process of 5-Hexenal, 3,3-dimethyl-4-(phenylmethoxy)-, (4S)-

There total 4 articles about 5-Hexenal, 3,3-dimethyl-4-(phenylmethoxy)-, (4S)- 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: 68.0%

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 570371-48-1
(S)-3-(benzyloxy)-2,2-dimethylpent-4-enal

: 570371-49-2
(4S)-4-benzyloxy-3,3-dimethyl-5-hexenal

Guidance literature:: (methoxymethyl)triphenylphosphonium chloride; With sec.-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

(S)-3-(benzyloxy)-2,2-dimethylpent-4-enal; In tetrahydrofuran; hexane; at 20 ℃; for 3h;

With toluene-4-sulfonic acid; In water; acetone; at 0 ℃; for 2h;
DOI:10.1016/S0040-4020(03)00297-7

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 570371-49-2
(4S)-4-benzyloxy-3,3-dimethyl-5-hexenal

Guidance literature:: Multi-step reaction with 2 steps

1.1: 310 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: sec-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: tetrahydrofuran; hexane / 3 h / 20 °C

2.3: 68 percent / TsOH / H₂O; acetone / 2 h / 0 °C

With oxalyl dichloride; sec.-butyllithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1016/S0040-4020(03)00297-7

Reference yield:

: 20374-33-8
(R)-(+)-3-(Benzyloxy)-4,5-dihydro-4,4-dimethyl-furan-2(3H)-on

: 570371-49-2
(4S)-4-benzyloxy-3,3-dimethyl-5-hexenal

Guidance literature:: Multi-step reaction with 4 steps

1.1: 484 mg / DIBAL / toluene / 2 h / -78 °C

2.1: BuLi / hexane; tetrahydrofuran

2.2: 323 mg / tetrahydrofuran; hexane / 3 h / 0 °C

3.1: 310 mg / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: sec-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

4.2: tetrahydrofuran; hexane / 3 h / 20 °C

4.3: 68 percent / TsOH / H₂O; acetone / 2 h / 0 °C

With n-butyllithium; oxalyl dichloride; sec.-butyllithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; toluene; 2.2: Wittig reaction / 3.1: Swern oxidation / 4.2: Wittig reaction;
DOI:10.1016/S0040-4020(03)00297-7