Methyl chloroformate → Ethyl 3-[3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphth-2-yl]propiolate

HRID 1636532

Reaktionsgleichung

[CH3:1][C:2]1([CH3:21])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[CH:4][C:3]1=2.[CH3:22]C1C(C#C)=CC2C(C)(C)CCC(C)(C)C=2C=1.COC(Cl)=O.C([Li])CCC>>[CH3:22][C:5]1[C:6]([C:14]#[C:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7][C:8]2[C:9]([CH3:12])([CH3:13])[CH2:10][CH2:11][C:2]([CH3:21])([CH3:1])[C:3]=2[CH:4]=1

Komponenten

Edukt 4

HCID 6586Methyl chloroformate

HCID 11000580Ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)propiolate2×

HCID 118063871,1,4,4,7-Pentamethyl-6-ethynyl-1,2,3,4-tetrahydronaphthalene

HCID 178418339Butyllithium

Produkt 1

HCID 18357952Ethyl 3-[3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphth-2-yl]propiolate

Versuchsvorschrift

Employing the same general procedure as used for the preparation of ethyl 3-[5,5,8,8,-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl]propiolate (Compound A), but instead using 1.9 g of (3-methyl-5,5,8,8,-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethyne, 940 mgs (10 mmols) of methylchloroformate and 8.8 mmols of n-butyllithium the title compound was obtained as an oil.

Quellen und Nachweise

ORD-Eintrag: ord-73389f9bfdf042e9913abfa3a502d261
Quelldatensatz: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06034242

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