Potassium Carbonate → [7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

HRID 38985

Reaktionsgleichung

Reaktionsgleichung von HRID 38985
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][OH:12])[O:7][C:6]=2[CH:13]=1.[CH3:14][S:15]([O-:17])=[O:16].[Na+].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[CH3:14][S:15]([C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][OH:12])[O:7][C:6]=2[CH:13]=1)(=[O:17])=[O:16]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 233965(7-Bromo-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanolHCID 2733271Sodium methanesulfinate

Produkt 1

HCID 66878354[7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanolAusbeute 182,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

4 batches of a mixture of (7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl)methanol (0.5 g, 2.0 mmol), sodium methanesulfinate (85%) (0.37 g, 3.1 mmol), CuI (0.039 g, 0.2 mmol), L-proline (0.047 g, 0.4 mmol) and K2CO3 (0.056 g, 0.4 mmol) in DMSO (4 ml) was heated under microwave radiation to 140° C. for 1 h in a nitrogen-flushed vial. The batches were mixed and diluted with water and HCl (1 N). The resulting solution was extracted with EtOAc. The combined organic phases were washed with brine, dried and purified on flash column chromatography (isooctane/EtOAc/MeOH) to give the title compound (0.89 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (40), 165 (27), 134 (22), 79 (18).

Aufarbeitung

  1. customflushed vial
  2. additionThe batches were mixed
  3. additiondiluted with water and HCl (1 N)
  4. extractionThe resulting solution was extracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. customdried
  7. custompurified on flash column chromatography (isooctane/EtOAc/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-3377528d9b854baa9fa119b59dfddfc1
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524766B2

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