Triphenylphosphine → HCID 58072009、化合物

HRID 870510ノート

反応式

HRID 870510 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>O1CCCC1.O>[O:33]1[CH2:38][CH2:37][CH:36]([O:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[C:10]([F:11])([F:12])[F:13])[CH2:35][CH2:34]1

参加物

7

反応物 4

HCID 11776Triphenylphosphine2 回HCID 74956Tetrahydro-4H-pyran-4-ol2 回HCID 27831594-Hydroxy-3-(trifluoromethyl)benzonitrileHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylate2 回

生成物 1

HCID 58072009HCID 58072009、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

2 g 4-Hydroxy-3-trifluoromethyl-benzonitrile, 5.6 g triphenylphosphine and 1.2 g tetrahydro-4H-pyran-4-ol was suspended in 15 mL tetrahydrofuran at 0° C. before 4.92 g di-tert-butylazodicarboxylate (DBAD) as a solution in 5 mL tetrahydrofuran was added over 15 min. The reaction was warmed to ambient temperature. Additional 2.8 g triphenylphosphine, 0.55 g (5.3 mmol) tetrahydro-4H-pyran-4-ol and 2.46 g di-tert-butylazodicarboxylate (DBAD) in tetrahydrofuran were added and the reaction was stirred overnight. After this time, the reaction was diluted with water and extracted with ethyl acetate (×2). The organic phase was separated and then it was washed with 2N sodium hydroxide, water and saturated sodium chloride, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel chromatography (SiO2: heptane/ethyl acetate) to provide the title compound.

後処理

  1. additionwas added over 15 min
  2. extractionextracted with ethyl acetate (×2)
  3. customThe organic phase was separated
  4. washit was washed with 2N sodium hydroxide, water and saturated sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified with silica gel chromatography (SiO2: heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-1b43951b297e4ff894af95918fc35668
出典データセット
uspto-grants-2015_03
特許番号
US08969568B2

反応ノート

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