4-Toluenesulfonyl chloride → (R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

HRID 926214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926214
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[C@@H:13]([OH:16])[CH2:14][OH:15].C([Sn](=O)CCCC)CCC.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.CCN(CC)CC>C(Cl)Cl>[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([O:15][CH2:14][C@@H:13]([C:3]2[C:4]([CH3:12])=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]=2[Cl:1])[OH:16])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Komponenten

6

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 61221Dibutyltin oxideHCID 89677395(R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

Produkt 1

HCID 89676690(R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of (R)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol (2.30 g, 9.74 mmol) in CH2Cl2 (97 mL), dibutyltinoxide (48.5 mg, 0.19 mmol), p-toluenesulfonyl chloride (2.08 g, 10.90 mmol), and Et3N (1.60 mL, 11.58 mmol) were added at room temperature). After stirring for 15 h, the reaction mixture was quenched with saturated aqueous NH4Cl, and then diluted with CH2Cl2. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (R)-2-(1-chloro-3-methylnaphthalen-2-yl)-2-hydroxyethyl 4-methylbenzenesulfonate. 1H-NMR: 400 MHz, (CDCl3) δ 8.18 (d, J=8.8 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.57-7.54 (m, 5H), 5.82 (t, J=5.6 Hz, 1H), 4.44 (dd, J=10.0, 6.8 Hz, 1H), 4.35 (dd, J=10.4, 5.6 Hz, 1H), 2.59 (s, 3H), 2.29 (s, 3H).

Aufarbeitung

  1. customthe reaction mixture was quenched with saturated aqueous NH4Cl
  2. additiondiluted with CH2Cl2
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7c4f5e5121ba4c3b84d23c4eef26f316
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284323B2

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