Tetrahydrofuran → (+/-)-6-Acetoxy-2,5,7,8-tetramethylchroman-2-carboxaldehyde

HRID 268429Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268429
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([C:18]#N)([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.[O:31]1CCCC1>>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:17])([CH:18]=[O:31])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 144156756-Acetoxy-2,5,7,8-tetramethyl-2-cyanochromaneHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 15818868(+/-)-6-Acetoxy-2,5,7,8-tetramethylchroman-2-carboxaldehyde

Versuchsvorschrift

(±)-6-acetoxy-2-cyano-2,5,7,8-tetramethylchroman was reduced with diisobutylaluminum hydride as described in Example 101, with tetrahydrofuran as reaction solvent. TLC of the crude product indicated that it was partially deacetylated. The material was thus reacetylated by the process described in Example 2 to give (±)-6-acetoxy-2,5,7,8-tetramethylchroman-2-carboxaldehyde as a white solid, m.p. 88°-90°, from 30°-60° petroleum ether.

Quellen und Nachweise

ORD-Eintrag
ord-efaa266f25fb4649907605182e398c8f
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03947473

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