Methyl 5-Iodosalicylate → rac-5-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethynyl]-2-hydroxybenzoic acid methyl ester

HRID 256840

Reaktionsgleichung

Reaktionsgleichung von HRID 256840
[C:1]([C:3]1([CH3:17])[CH2:8][CH2:7][C:6]2[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=2[O:4]1)#[CH:2].[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25](I)[CH:24]=[CH:23][C:22]=1[OH:28]>C(Cl)Cl>[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([C:2]#[C:1][C:3]2([CH3:17])[CH2:8][CH2:7][C:6]3[C:9]([CH3:16])=[C:10]([OH:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:5]=3[O:4]2)[CH:24]=[CH:23][C:22]=1[OH:28]

Komponenten

4

Edukt 2

HCID 248910Methyl 5-IodosalicylateHCID 14478563rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6ol

Produkt 1

HCID 15171827rac-5-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethynyl]-2-hydroxybenzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

rac-5-[(3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)ethynyl]-2-hydroxybenzoic acid methyl ester was prepared by reacting rac-3,4-dihydro-2-ethynyl-2,5,7,8-tetramethyl-2H-1-benzopyran-6-ol with 2-hydroxy-5-iodobenzoic acid methyl ester [M. Covello, Chim. Ther. 2, 73 (1967)] as described in Example 4. The compound was isolated by chromatography over silica gel using methylene chloride and was crystallized from ethyl acetate/hexane to yield colorless crystals with m.p. 151°-153° C.

Aufarbeitung

  1. customThe compound was isolated by chromatography over silica gel
  2. customwas crystallized from ethyl acetate/hexane
  3. customto yield colorless crystals with m.p. 151°-153° C.

Quellen und Nachweise

ORD-Eintrag
ord-89f0dbfe8aa048e0a28b24d2494b3f77
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260294

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