Triethylamine → 6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one

HRID 2173422

반응식

HRID 2173422 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][C@H:6]([CH3:13])[CH2:5]2.[CH2:14](N(CC)CC)[CH3:15].C([B-](F)(F)F)=C.[K+]>CCO.C(Cl)(Cl)Cl>[CH:14]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[O:7][CH:6]([CH3:13])[CH2:5]2)=[CH2:15]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 71270763(3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one

생성물 1

HCID 675177156-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6212Chloroform용매

반응 조건

온도
100 °C

실험 절차

A solution of (3R)-6-bromo-3-methyl-3,4-dihydro-1H-isochromen-1-one (2.4 g, 9.96 mmol) and triethylamine (2.78 ml, 19.91 mmol) in EtOH (39.8 ml) was added to a microwave vial containing Cl2Pd(dppf)2-DCM (0.406 g, 0.498 mmol) and potassium vinyltrifluoroborate (2,000 g, 14.93 mmol). The contents of the vial were heated to 100° C. for 1 hour after which the mixture was cooled, diluted with chloroform (50 mL) and washed with aqueous ammonium chloride (25 mL). The organic layer was then dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. MPLC purification (15-60% EtOAc/Hex) gave 6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one. 1H NMR (500 MHz; CDCl3): 8.07 (d, J=8.0 Hz, 1H), 7.44 (dd, J=1.2, 7.1 Hz, 1H), 7.26 (s, 1H), 6.75 (dd, J=10.8, 17.6 Hz, 1H), 5.90 (d, J=17.6 Hz, 1H), 5.44 (d, J=11 Hz, 1H), 4.75 (m, 1H), 2.96 (m, 2H), 1.54 (d, J=6.1 Hz, 3H); LC/MS (M+H)+189;

후처리

  1. temperaturewas cooled
  2. washwashed with aqueous ammonium chloride (25 mL)
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customMPLC purification (15-60% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-43fe3ee364fc4a8d953f97a7e7aa1e00
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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