Sodium Hydroxide → [(2S)-7-(Methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methanol

HRID 38995

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of [(2S)-7-bromo-2,3-dihydro-1,4-benzodioxin-2-yl]methanol (0.6 g, 2.3 mmol), sodium methanesulfinate (85%) (0.4 g, 3.4 mmol), CuI (0.043 g, 0.2 mmol), L-proline (0.052 g, 0.5 mmol) and NaOH (0.018 g, 0.5 mmol) in DMSO (3 ml) was heated under microwave radiation at 140° C. for 2 h 30 min in a nitrogen-flushed vial. The mixture was mixed with 2 other batches and water and EtOAc was added. The solution was extracted with EtOAc (3×50 ml). The combined organic phases were washed with LiCl (5%), HCl (1 N) and brine. The resulting solution was dried (Na2SO4) and evaporated to dryness. Purification on flash column chromatography (isooctane/EtOAc) gave the title compound (1.2 g). MS m/z (rel. intensity, 70 eV) 244 (M+, bp), 213 (39), 165 (26), 134 (22), 79 (23).

Workup

customflushed vial
additionThe mixture was mixed with 2 other batches and water and EtOAc
additionwas added
extractionThe solution was extracted with EtOAc (3×50 ml)
washThe combined organic phases were washed with LiCl (5%), HCl (1 N) and brine
dry with materialThe resulting solution was dried (Na2SO4)
customevaporated to dryness
customPurification on flash column chromatography (isooctane/EtOAc)

Sources & evidence

ORD record: ord-03f4373c7a4a4431bff4e8401daf1f70
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Linked notes

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