Triethylamine → HCID 66969799、化合物

HRID 1510299ノート

反応式

HRID 1510299 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:12][C@@H:13]([CH3:17])[CH2:14][O:15][CH3:16])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][O:15][CH2:14][C@H:13]([CH3:17])[O:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([O:1][C:22]2[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 2856454-Fluorophenylboronic acidHCID 59127146methyl 3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoate

生成物 1

HCID 66969799HCID 66969799、化合物

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of methyl 3-hydroxy-5-[(1S)-2-methoxy-(1-methylethyl)oxy]benzoate (3.53 g, 14.7 mmol), p-fluoro-phenyl-boronic acid (16.2 mmol), copper(II) acetate (2.94 g, 16.2 mmol), triethylamine (10.3 ml, 73.5 mmol) and freshly activated 4A molecular sieves (17.7 g) in dichloromethane was stirred at ambient temperature and under ambient atmosphere for 2 days. The reaction mixture was filtered, and the dichloromethane was removed in vacuo. The residual oil was partitioned between ethyl acetate and 2 mol/l hydrochloric acid. The ethyl acetate layer was separated, washed with aqueous sodium hydrogen carbonate and brine, dried over Na2SO4 and evaporated to give a residue, which was purified by column chromatograph on silica gel (20-60% ethyl acetate in iso-hexane, gradient) to give the desired ester.

後処理

  1. filtrationThe reaction mixture was filtered
  2. customthe dichloromethane was removed in vacuo
  3. customThe residual oil was partitioned between ethyl acetate and 2 mol/l hydrochloric acid
  4. customThe ethyl acetate layer was separated
  5. washwashed with aqueous sodium hydrogen carbonate and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto give a residue, which
  9. customwas purified by column chromatograph on silica gel (20-60% ethyl acetate in iso-hexane, gradient)

出典と根拠

ORDレコード
ord-9853352328fb4e0690e5f6ca34b7b9d5
出典データセット
uspto-grants-2012_07
特許番号
US08211925B2

反応ノート

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