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

HRID 2173417

반응식

HRID 2173417 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

A sealed tube was charged with aryl bromide, palladium(II) acetate (0.028 g, 0.124 mmol) and tri-t-butylphosphine-BF4 complex (0.072 g, 0.249 mmol) and sealed. The tube was evacuated and refilled with nitrogen before DMF (12.44 ml) and (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one (0.75 g, 3.11 mmol) were added followed by bromo(1,3-dioxolan-2-ylmethyl)zinc (6.22 ml, 3.11 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. 1H NMR (500 MHz; CDCl3): 8.04 (d, J=7.8 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.17 (s, 1H), 5.11 (1, J=4.7 Hz, 1H), 4.68 (m, 1H), 3.96 (m, 2H), 3.88 (m, 2H), 3.03 (d, J=4.9 Hz, 2H), 2.93 (m, 2H), 1.54 (d, J=6.4 Hz, 3H); LC-MS (IE, m/z): 249 [M+1]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-b04b9e2987ec4a5283f269e3fb281d1e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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