Triphenylphosphine → 3-Tert-butyl-4-(2-morpholin-4-ylethoxy)benzaldehyde

HRID 1860807

반응식

HRID 1860807 반응식
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]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 30176183-(tert-Butyl)-4-hydroxybenzaldehydeHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 225710723-Tert-butyl-4-(2-morpholin-4-ylethoxy)benzaldehyde수율 44%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. concentrationThe reaction was concentrated under reduced pressure
  2. custompartitioned between 2N hydrochloric acid (200 ml) and ethyl acetate (150 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×150 ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-316212f9b7a04b65978e30c516af77eb
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531502B1

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