Acetonitrile → Dibutyl phenylphosphonate

HRID 1498983ノート

反応式

HRID 1498983 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Si](C)(C)C)(=O)=O.[F-].[Cs+].[P:21]([O:32]CCCC)([O:27][CH2:28][CH2:29][CH2:30][CH3:31])[O:22][CH2:23][CH2:24][CH2:25][CH3:26].C(#N)C>CCOC(C)=O>[C:7]1([P:21](=[O:32])([O:27][CH2:28][CH2:29][CH2:30][CH3:31])[O:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 7623Tributyl phosphiteHCID 25953Cesium fluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonate

生成物 1

HCID 70559Dibutyl phenylphosphonate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

2-(trimethylsilyl)phenyl trifluoromethanesulfonate (25 mg, 0.083 mmol), Cesium Fluoride (70 mg, 0.461 mmol), Tributyl phosphite (83 mg, 0.335 mmol), Acetonitrile (1 ml): Reaction Time: 24 h; Rf: 0.4 (1:3 EtOAc:Pet. Ether); Thick oil; 16.3 mg, 72%; 1H NMR (400 MHz, CDCl3, TMS) δ 7.80 (dd, J=6.8, 13.3 Hz, 2H), 7.55 (t, J=7.5 Hz, 1H), 7.50-7.42 (m, 2H), 4.12-3.95 (m, 4H), 1.65 (quint, J=7.3 Hz, 4H), 1.39 (sext, J=7.3 Hz, 4H), 0.9 (t, J=7.3 Hz, 6H); 13C NMR (100 MHz, CDCl3, TMS) δ 132.3 (d, J=3.1 Hz), 131.7 (d, J=9.3 Hz), 128.4 (d, J=15.4 Hz), 128.3 (d, J=187.3 Hz), 65.8 (d, J=5.4 Hz), 32.4 (d, J=6.9 Hz), 18.7, 13.6; 31P NMR (162 MHz, CDCl3) δ 18.8; Mass (M+Na)+ 293; Known compound, Lit. X. Lu, J. Zhu, Synthesis 1987, 8, 726.

後処理

  1. custom24 h
  2. customZhu, Synthesis 1987, 8, 726

出典と根拠

ORDレコード
ord-abe7252d9e6941abbc2384ee5dbdf668
出典データセット
uspto-grants-2015_12
特許番号
US09200018B2

反応ノート

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