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Hydrochloric Acid → Tert-butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoate

HRID 1007862
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1007862
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].Cl.[CH2:11]([O:18][CH2:19][C:20]1[C:21]([O:30][CH3:31])=[N:22][CH:23]=[CH:24][C:25]=1[C:26](=[O:29])[CH2:27][CH3:28])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1.[Zn]>[CH2:11]([O:18][CH2:19][C:20]1[C:21]([O:30][CH3:31])=[N:22][CH:23]=[CH:24][C:25]=1[C:26]([OH:29])([CH2:27][CH3:28])[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 79177tert-Butyl bromoacetateHCID 105411281-(3-Benzyloxymethyl-2-methoxy-pyridin-4-yl)-propan-1-one

Produkt 1

HCID 10834902Tert-butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-butyl bromoacetate (13 ml, 80 mmol) is added dropwise to a zinc suspension (5.3 g, 80 mmol activated with 6N HCl over 10 seconds, then washed successively with water until a neutral pH is achieved, with acetone and with diethyl ether) in anhydrous tetrahydrofuran (60 ml) under reflux. The reaction medium is maintained under reflux for another 10 minutes after the addition is terminated. Then, a solution of 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone (5.8 g, 20 mmol) in anhydrous tetrahydrofuran (20 ml) is added and the reaction mixture is agitated under reflux for another hour. The reaction is stopped at 0° C. with saturated aqueous ammonium chloride (100 ml) and the reaction mixture is extracted with diethyl ether. The combined extracts are dried over sodium sulphate and evaporated, which produces a yellow oil which is purified by column chromatography (SiO2, TBMO/HX: 5/95 to 10/90) in order to obtain the tert-butyl ester (J) (7 g, 95%) in the form of a limpid liquid.

Aufarbeitung

  1. washwashed successively with water until a neutral pH
  2. temperatureunder reflux
  3. temperatureThe reaction medium is maintained
  4. temperatureunder reflux for another 10 minutes
  5. additionafter the addition
  6. customis terminated
  7. temperatureunder reflux for another hour
  8. extractionthe reaction mixture is extracted with diethyl ether
  9. dry with materialThe combined extracts are dried over sodium sulphate
  10. customevaporated
  11. customwhich produces a yellow oil which
  12. customis purified by column chromatography (SiO2, TBMO/HX: 5/95 to 10/90) in order

Quellen und Nachweise

ORD-Eintrag
ord-5e6a206c6e4042338c07002ba77ce101
Quelldatensatz
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06797715B1

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