Methanesulfonyl chloride → Ethyl 2-(1-hydroxy-4-methyl-6-(methylsulfonyloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798136
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1.CCN(C(C)C)C(C)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12][S:29]([CH3:28])(=[O:31])=[O:30])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:3]1

Komponenten

5

Edukt 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Produkt 1

HCID 58292870Ethyl 2-(1-hydroxy-4-methyl-6-(methylsulfonyloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (500 mg, 2 mmol), DIPEA (774 mg, 6 mmol) in DCM (10 mL) was slowly added MsCl (366 mg, 3.2 mmol) at −78° C. The reaction mixture was stirred overnight at room temperature, quenched with saturated NH4Cl and washed with saturated NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was used directly in next step reaction without further purification. MS (ESI) m/z=329 [M+H]+

Aufarbeitung

  1. customat −78° C
  2. customquenched with saturated NH4Cl
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was used directly in next step reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-3d438335609c4777b2fcba36f1361e50
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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