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

HRID 253429

Reaction equation

HRID 253429 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-851efc62a6a34550ae20dfc6323d7fbe
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Linked notes

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