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

HRID 1501945ノート

反応式

HRID 1501945 の反応式
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.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(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][C@H:6]([CH3:13])[CH2:5]2)=[CH2:15]

参加物

7

反応物 3

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

生成物 1

HCID 86727028(3R)-6-ethenyl-3-methyl-3,4-dihydro-1H-isochromen-1-one

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

反応条件

温度
100 °C

実験手順

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 PdCl2(dppf)-CH2Cl2, (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 the title compound.

後処理

  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)

出典と根拠

ORDレコード
ord-75f27879dd2c4c20a5a8b4bb2c8a7392
出典データセット
uspto-grants-2015_12
特許番号
US09206199B2

反応ノート

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