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

HRID 38985

Reaction equation

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]

Participants

Conditions

Temperature: 140 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-3377528d9b854baa9fa119b59dfddfc1
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Linked notes

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