Veratryl alcohol → Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoate

HRID 2099958

Reaktionsgleichung

Reaktionsgleichung von HRID 2099958
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][OH:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1O)[C:17]([O:19][CH3:20])=[O:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][O:12][C:23]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[Cl:13]

Komponenten

6

Edukt 4

HCID 7118Veratryl alcoholHCID 11776TriphenylphosphineHCID 77580Methyl 3-chloro-4-hydroxybenzoateHCID 5462977Diethyl azodicarboxylate

Produkt 1

HCID 57796893Methyl 4-(3,4-dimethoxybenzyloxy)-3-chlorobenzoateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of (3,4-dimethoxyphenyl)methanol (6.0 g, 40 mmol) (Aldrich Chemical Co., Milwaukee, Wis.) and methyl 3-chloro-4-hydroxybenzoate (2.5 g, 13.5 mmol) (Lancaster Synthesis Ltd, Windham, N.H.) in THF (100 mL) was cooled to 0° C. and treated with triphenylphosphine (8.8 g, 33.5 mmol). A solution of diethylazodicarboxylate (5.3 mL, 33.5 mmol) in THF (50 mL) was added dropwise over 30 minutes. After the addition was complete, the reaction was warmed to room temperature and stirred for an additional 30 minutes, and then concentrated to orange oil. The crude reaction was applied directly to a silica column and flushed with hexanes. The desired product was eluted from the column using 25% EtOAc in Hexanes to afford 1A as a light yellow solid (2.5 g, 56%).

Aufarbeitung

  1. additionAfter the addition
  2. concentrationconcentrated to orange oil
  3. customThe crude reaction
  4. customflushed with hexanes
  5. washThe desired product was eluted from the column

Quellen und Nachweise

ORD-Eintrag
ord-d1f4d470a1d74677a7686f33a9dd5b5f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569725B2

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