Triphenylphosphine → Ethyl (2R)-2-[4-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenoxy]-3-phenylpropanoate

HRID 1072709ノート

反応式

HRID 1072709 の反応式
[CH2:1]([N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O[C@@H:27]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]([O:30][CH2:31][CH3:32])=[O:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH2:1]([N:13]1[C:17]([CH3:18])=[CH:16][CH:15]=[C:14]1[C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:27]([CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:21][CH:20]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9877619Ethyl phenyllactate, (-)-HCID 223877044-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenol

生成物 1

HCID 86588892Ethyl (2R)-2-[4-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenoxy]-3-phenylpropanoate収率 33%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 4-(1-dodecyl-5-methyl-1H-pyrrol-2-yl)phenol (2.97 g, 8.70 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.86 g, 9.58 mmol) and triphenylphosphine (2.51 g, 9.57 mmol) in toluene (120 ml) was added diethyl azodicarboxylate (1.67 g, 9.57 mmol) and the mixture was refluxed for 20 hours under heating. The insoluble matter was filtered out and the filtrate was diluted with ethyl acetate. The obtained solution was washed with water and dried over magnesium sulfate anhydride, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to give the object compound as an oily substance. 1.49 g (yield: 33%)

後処理

  1. temperaturethe mixture was refluxed for 20 hours
  2. temperatureunder heating
  3. filtrationThe insoluble matter was filtered out
  4. additionthe filtrate was diluted with ethyl acetate
  5. washThe obtained solution was washed with water
  6. dry with materialdried over magnesium sulfate anhydride
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=8:1)
  9. customto give the object compound as an oily substance

出典と根拠

ORDレコード
ord-f0d5fc47f90543568b514435fc4df75c
出典データセット
uspto-grants-2005_06
特許番号
US06911468B2

反応ノート

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