18-Crown-6 → Methyl 3-(3-cyanophenyl)prop-2-enoate

HRID 2184898

反応式

HRID 2184898 の反応式
P(=O)([O-])O[C:3]([CH2:13][C:14](F)(F)F)(CC(F)(F)F)[C:4]([O:6][CH3:7])=[O:5].C1OCCOCCOCCOCCOCCOC1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:48]([C:50]1[CH:51]=C([CH:55]=[CH:56][CH:57]=1)C=O)#[N:49]>C1COCC1.CCOC(C)=O.CCCCCC>[C:48]([C:50]1[CH:51]=[C:14]([CH:55]=[CH:56][CH:57]=1)[CH:13]=[CH:3][C:4]([O:6][CH3:7])=[O:5])#[N:49]

参加物

7

反応物 4

HCID 2855718-Crown-6HCID 90670m-FormylbenzonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178500451HCID 178500451、化合物

生成物 1

HCID 53396017Methyl 3-(3-cyanophenyl)prop-2-enoate収率 68.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

実験手順

To a solution of bis(2,2,2-trifluoroethyl)(methoxycarbonylmethyl) phosphonate (1.00 g, 3.14 mmol) and 18-crown-6 (4.14 g, 15.7 mmol) in THF (50 mL) at −78 C, potassium bis(trimethylsilyl)amide (6.3 mL, 0.5 M in toluene, 3.15 mmol) was added dropwise. After the addition was completed, 3-cyanobenzaldehyde (0.412 g, 3.14 mmol) in THF (8 mL) was added. The mixture was stirred at −78 C for 30 min before it was quenched with aq. NH4Cl. Water and ether were added. Aqueous phase was separated, extracted with ether once more. The combined organic solutions were dried over Na2SO4, concentrated in vacuo to give a solid, which was purified by a silica gel column, first eluted with EtOAc/hexane (5/95), then with EtOAc/hexane (10/90) to give the titled compound (0.40 g) (yield: 68%). 1H NMR (CDCl3) 7.85 (s, 1H), 7.77 (d, 1H, J=8 Hz), 7.60 (d, 1H, J=8 Hz), 7.45 (t, 1H, J=8 Hz), 6.91 (d, 1H, J=12 Hz), 6.06 (d, 1H, J=12 Hz).

後処理

  1. additionAfter the addition
  2. customwas quenched with aq. NH4Cl
  3. additionWater and ether were added
  4. customAqueous phase was separated
  5. extractionextracted with ether once more
  6. dry with materialThe combined organic solutions were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give a solid, which
  9. customwas purified by a silica gel column
  10. washfirst eluted with EtOAc/hexane (5/95)

出典と根拠

ORDレコード
ord-57f5192d728a4a3e8f6b70f7381216e3
出典データセット
uspto-grants-2002_06
特許番号
US06399627B1

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