Hexane → Pentafluorophenyl 2-allyloxymethyl-3-methoxybenzoate

HRID 229957

反応式

HRID 229957 の反応式
[CH2:1]([O:4][CH2:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])[CH:2]=[CH2:3].[F:17][C:18]1[C:23](O)=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28].C1CCC(N=C=NC2CCCCC2)CC1.CCCCCC>C(OCC)(=O)C>[CH2:1]([O:4][CH2:5][C:6]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([O:10][C:23]1[C:22]([F:25])=[C:21]([F:26])[C:20]([F:27])=[C:19]([F:28])[C:18]=1[F:17])=[O:9])[CH:2]=[CH2:3]

参加物

6

反応物 4

HCID 8058HexaneHCID 10868Dicyclohexylcarbodiimide2 回HCID 13041PentafluorophenolHCID 598386492-Allyloxymethyl-3-methoxy benzoic acid

生成物 1

HCID 59838640Pentafluorophenyl 2-allyloxymethyl-3-methoxybenzoate収率 110%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒3 回

実験手順

Into a 200 mL round bottom flask was added 6.6 g (0.0297 mol) of 2-allyloxymethyl-3-methoxy benzoic acid and 40 mL of ethyl acetate. 24.05 g of a 25% pentafluorophenol (6.01 g, 0.0327 mol) solution in ethyl acetate was added while stirring. The reaction flask was placed into a water bath and while stirring small portions of DCC (6.2 g, 0.030 mol) were added. The stirring continued overnight at room temperature. The reaction was filtered through two Whatman #541 filters to remove the DCU precipitate. The ethyl acetate solution was concentrated to yield 12.8 g (110% yield), indicating presence of DCC and DCU. This was confirmed by TLC (1:1 ethyl acetate:hexane), which indicated a Rf of 0.72 plus other less polar compounds (12 stain indicates about 85% purity). 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.7 (d, 1H), 7.45 (t, 1H), 7.15 (d, 1H), 6.0-5.9 (m, 1H), 5.3-5.1 (2d, 2H), 4.88-4.83 (d, 2H), 4.06 (d, 2H), 3.90 (s, 3H).

後処理

  1. customThe reaction flask was placed into a water bath
  2. additionwere added
  3. customThe stirring continued overnight
  4. customat room temperature
  5. filtrationThe reaction was filtered through two Whatman #541 filters
  6. customto remove the DCU precipitate
  7. concentrationThe ethyl acetate solution was concentrated
  8. customto yield 12.8 g (110% yield)

出典と根拠

ORDレコード
ord-b89bdfbf7ebd473592f3dd5f48ad5aff
出典データセット
uspto-grants-2009_07
特許番号
US07563928B2

関連ノート

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