Dimethylformamide → 8-Methyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde

HRID 639031Notes

Reaction equation

Br[C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[CH:3]=1.[CH3:14]N(C=O)C>[F-].[K+]>[CH3:14][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=[C:4]([CH:12]=[O:13])[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 8-bromo-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde (240 mg, 0.987 mmol) in DMF (5 mL) were added LiCL (126 mg, 2.96 mmol), Me Sn (0.137 mL, 0.987 mmol) and PdCL2(PPh)2 (35 mg, 0.049 mmol). After heated at 70° C. for 12 hr, the mixture was cooled down to room temperature and diluted with aqueous KF solution. The resulting solution was extracted several times with DCM. The organic parts were combined, concentrated and purified with column chromatography (silica, 10-40% Ethyl acetate in hexane) affording the title compound as an off-white solid (145 mg, 83%): MS (ES) m/z 179 (M+H)+.

Workup

temperaturethe mixture was cooled down to room temperature
extractionThe resulting solution was extracted several times with DCM
concentrationconcentrated
custompurified with column chromatography (silica, 10-40% Ethyl acetate in hexane)

Sources & evidence

ORD record: ord-d9d90dc5a40042f08d047cdbe41771eb
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691850B2

Reaction notes

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