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

HRID 253429

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HRID 253429 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-851efc62a6a34550ae20dfc6323d7fbe
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872018B2

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