Lithium Hexamethyldisilazide → Methyl 4-{2-(3-bromophenyl)-3-[(4-methoxybenzyl)oxy]-1-methyl-3-oxopropyl}benzoate

HRID 2246892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2246892
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[O:20])[CH:15]=[CH:16][CH:17]=1.Br[CH:32]([C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)[CH3:33]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([CH:18]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[O:20])[CH:32]([C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)[CH3:33])[CH:15]=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 12342351Methyl 4-(1-bromoethyl)benzoateHCID 866195534-Methoxybenzyl (3-bromophenyl)acetate

Produkt 1

HCID 67262891Methyl 4-{2-(3-bromophenyl)-3-[(4-methoxybenzyl)oxy]-1-methyl-3-oxopropyl}benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

LHMDS (1.0M THF, 2.6 mL) was added dropwise to a −78° C. THF (4 mL) solution containing the intermediate from Step A (0.827 g, 2.47 mmol). After stirring 10 minutes a THF (4 mL) solution containing methyl 4-(1-bromoethyl)benzoate (0.6 g, 2.47 mmol) was added dropwise. The solution was allowed to warm to room temperature. After 1.5 hours the solution was partitioned between ethyl acetate and aqueous 1N HCl. The organic phase was washed with water, brine and dried over magnesium sulfate. The solution was filtered and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compounds as a 1.67/1 mixture of diastereomers. 1H NMR (400 MHz, CDCl3): selected data δ 5.16 (d, J=12.0 Hz); 5.01 (d, J=12.0 Hz); 4.82 (d, J=12.0 Hz); 4.64 (d, J=11.9 Hz); 1.34 (d, J=6.8 Hz); 1.02 (d, J=7.0 Hz). Minor diastereomer: LCMS1 4.08 min (M+Na)=519. Major diastereomer: LC1 4.19 min (M+Na)=519.

Aufarbeitung

  1. additionwas added dropwise
  2. customAfter 1.5 hours the solution was partitioned between ethyl acetate and aqueous 1N HCl
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe residue purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-107f6785369f41f9b2d38efe4db22efd
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07687534B2

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