Boron trifluoride → 3-Cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester

HRID 2360580ノート

反応式

HRID 2360580 の反応式
[C:1](O)(=[O:3])C.C(O)(=O)C.I(C1C=CC=CC=1)=O.B(F)(F)F.[CH2:21]([O:23][C:24](=[O:33])[CH2:25][C:26]([CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27])C>CO>[CH3:21][O:23][C:24](=[O:33])[CH:25]([O:3][CH3:1])[C:26]([CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27]

参加物

5

反応物 3

HCID 6356Boron trifluorideHCID 11159709Ethyl 3-cyclopentyl-3-oxopropanoateHCID 73357407Acetic acid;iodosylbenzene

生成物 1

HCID 597772863-Cyclopentyl-2-methoxy-3-oxo-propionic acid methyl ester

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The title compound was prepared using a method analogous to that described in Tetrahedron 1998, 44, 1603-1607: To a suspension of iodosobenzene diacetate (5.2 g, 16.3 mmol) in MeOH (40 mL) was added BF3.0Et2 (2.1 mL, 16.3 mmol). The resulting mixture was added to 3-cyclopentyl-3-oxo-propionic acid ethyl ester (3.0 g, 16.3 mmol) and stirred at rt overnight. The mixture was concentrated to half the total volume, quenched with satd. aq. NaHCO3, and extracted with CHCl3 (2×). The combined organic layers were dried and concentrated and the crude residue purified (EtOAc/hexanes) to yield a colorless oil (1.5 g, 43%). 1H NMR (MeOD): 4.4 (s, 1H), 3.8 (s, 3H), 3.5 (s, 3H), 3.3-3.2 (m, 1H), 1.9-1.5 (m, 8H).

後処理

  1. concentrationThe mixture was concentrated to half the total volume
  2. customquenched with satd
  3. extractionaq. NaHCO3, and extracted with CHCl3 (2×)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe crude residue purified (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-67374e29976643d285c7ad4bdfe39613
出典データセット
uspto-grants-2014_04
特許番号
US08686142B2

反応ノート

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