Dimethylformamide → (3R)-6-(1,3-dioxolan-2-ylmethyl)-3-methyl-3,4-dihydro-1H-isochromen-1-one

HRID 2281305Notes

Reaction equation

HRID 2281305 reaction equation
CN(C=O)C.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][C@H:11]([CH3:18])[CH2:10]2.Br[Zn][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:23]1[CH2:24][CH2:25][O:26][CH:22]1[CH2:21][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[O:12][C@H:11]([CH3:18])[CH2:10]2

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 71270763(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-oneHCID 178419777HCID 178419777, compound

Product 1

HCID 86693034(3R)-6-(1,3-dioxolan-2-ylmethyl)-3-methyl-3,4-dihydro-1H-isochromen-1-one

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A sealed tube was charged with aryl bromide, palladium(II) acetate (0.028 g, 0.124 mmol) and commercially available tri-t-butylphosphine-BF4 complex (0.072 g, 0.25 mmol) and sealed. The tube was evacuated and refilled with nitrogen before DMF (12 ml) and (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one (0.75 g, 3.1 mmol) were added followed by commercially available bromo(1,3-dioxolan-2-ylmethyl)zinc (6.2 ml, 3.1 mmol). The tube was heated to 110° C. in the microwave for 75 minutes, after which it was cooled, diluted with EtOAc, filtered, concentrated and purified via MPLC (20-50% E/H) to afford (3R)-6-(1,3-dioxolan-2-ylmethyl)-3-methyl-3,4-dihydro-1H-isochromen-1-one.

Workup

  1. customsealed
  2. customThe tube was evacuated
  3. additionwere added
  4. temperatureafter which it was cooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via MPLC (20-50% E/H)

Sources & evidence

ORD record
ord-a47bf1f66d57484a9c3c1328e0c18da4
Source dataset
uspto-grants-2015_09
Patent number
US09139585B2

Reaction notes

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