Triphenylphosphine → 4-(3-Diethylamino-propoxy)-2-fluoro-5-methoxy-benzaldehyde

HRID 253429

反応式

HRID 253429 の反応式
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([O:11][CH3:12])=[CH:6][C:3]=1[CH:4]=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:32]([N:34]([CH2:39][CH3:40])[CH2:35][CH2:36][CH2:37]O)[CH3:33].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[CH2:32]([N:34]([CH2:39][CH3:40])[CH2:35][CH2:36][CH2:37][O:10][C:8]1[C:7]([O:11][CH3:12])=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([F:1])[CH:9]=1)[CH3:33]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 121593-(Diethylamino)-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5981552-Fluoro-4-hydroxy-5-methoxybenzaldehyde

生成物 1

HCID 580874184-(3-Diethylamino-propoxy)-2-fluoro-5-methoxy-benzaldehyde

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To 2-fluoro-4-hydroxy-5-methoxy-benzaldehyde (39, 1.20 g, 7.05 mmol, prepared as described in Scheme 12 of Example 15) in tetrahydrofuran (60.0 mL) were added triphenylphosphine (1.93 g, 7.35 mmol) and 3-(diethylamino)-propan-1-ol, (0.96 g, 7.30 mmol). The reaction was cooled to 0° C., followed by slow addition of diethyl azodicarboxylate (1.28 g, 7.35 mmol). The reaction was allowed to warm to room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 10% methanol in dichloromethane to give a colorless oil (102, 0.90 g, 45.0%).

後処理

  1. temperatureto warm to room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 10% methanol in dichloromethane
  8. customto give a colorless oil (102, 0.90 g, 45.0%)

出典と根拠

ORDレコード
ord-851efc62a6a34550ae20dfc6323d7fbe
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

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