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Hydrochloric Acid → (R)-Methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)acetate

HRID 633475
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 633475
[OH:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])[C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1)([O-:23])=[O:22].Cl>CN(C)C1C=CN=CC=1.ClCCl>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([S:30]([O:1][C@H:2]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:3]([O:5][CH3:6])=[O:4])(=[O:32])=[O:31])=[CH:28][CH:29]=1)([O-:23])=[O:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 11790232(R)-Methyl 2-(2-chlorophenyl)-2-hydroxyacetate

Produkt 1

HCID 45114280(R)-Methyl 2-(2-chlorophenyl)-2-(4-nitrophenylsulfonyloxy)acetateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.72 g (6 mmoles; 0.1 equivalent) of 4-dimethylaminopyridine, 12.0 g (60 mmoles; 1 equivalent) of methyl(R)-2-hydroxy-2(2-chlorophenyl)acetate and 7.8 g (78 mmoles; 1.3 equivalent) of triethylamine and 20 ml of dichloromethane were added to a dry reaction flask. The colorless solution obtained was cooled to 0° C. and then, operating at this temperature, 13.14 g (60 mmoles; 1 equivalent) of 4-nitrobenzenesulfonyl chloride as a solution in 30 ml of dichloromethane was added. The reaction mixture was stirred for 3 hours at 0° C. and 240 ml of 1N hydrochloric acid and 240 ml of dichloromethane was added drop wise, while stirring this mixture. After decanting, the dichloromethane phase is washed with dilute hydrochloric acid and then with water, before being concentrated under reduced pressure. An analytically pure sample is obtained after purifying on a silica column. In this manner, methyl(R)-2-(4-nitrophenylsulfonyloxy)-2(2-chlorophenyl)acetate is obtained: Yield: 98%. Optical purity: 99%.

Aufarbeitung

  1. customThe colorless solution obtained
  2. additionwas added
  3. stirringwhile stirring this mixture
  4. customAfter decanting
  5. washthe dichloromethane phase is washed with dilute hydrochloric acid
  6. concentrationwith water, before being concentrated under reduced pressure
  7. customAn analytically pure sample is obtained
  8. customafter purifying on a silica column

Quellen und Nachweise

ORD-Eintrag
ord-7fff9e5a18f744c89870a6e81b8041c9
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321785B2

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