Triphenylphosphine → 3-Tert-butyl-4-(2-morpholin-4-ylethoxy)benzaldehyde
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[OH:32])[CH:27]=[O:28])([CH3:23])([CH3:22])[CH3:21].O[CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:20]([C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[O:32][CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1)[CH:27]=[O:28])([CH3:23])([CH3:21])[CH3:22]Participants
Procedure
Triphenylphosphine (5.89 g, 22.44 mmol) was added to a solution of 3-tert-butyl-4-hydroxybenzaldehyde (4 g, 22.44 mmol) in tetrahydrofuran (40 ml), followed by addition of 2-hydroxyethylmorpholine (2.94 g, 22.44 mmol) and then the dropwise addition of diethylazodicarboxylate (3.91 g, 22.44 mmol). The mixture was allowed to stir at room temperature for 3 days. The reaction was concentrated under reduced pressure and partitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml). The aqueous layer was extracted with ethyl acetate (2×150 ml), basified to pH 9 with solid sodium bicarbonate, saturated with solid sodium chloride and extracted with ethyl acetate (3×150 ml). The combined organic layers were dried over magnesium sulfate and concentrated to afford 2.8 g (44%) of 3-tert-butyl-4-(2-morpholin-4-ylethoxy)benzaldehyde as a yellowish oil.
Workup
- concentrationThe reaction was concentrated under reduced pressure
- custompartitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml)
- extractionThe aqueous layer was extracted with ethyl acetate (2×150 ml)
- extractionextracted with ethyl acetate (3×150 ml)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-316212f9b7a04b65978e30c516af77eb
- Source dataset
- uspto-grants-2003_03
- Patent number
- US06531502B1
Reaction notes
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