Triphenylphosphine → 3,5-Diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

HRID 24377

反応式

HRID 24377 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]([C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([CH:32]([CH3:34])[CH3:33])[C:30]=1[OH:31])[CH:26]=[O:27])([CH3:22])[CH3:21].O[CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:20]([C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([CH:32]([CH3:34])[CH3:33])[C:30]=1[O:31][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1)[CH:26]=[O:27])([CH3:22])[CH3:21]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 827124-Hydroxy-3,5-bis(isopropyl)benzaldehydeHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 225711303,5-Diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde収率 14.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triphenylphosphine (5.14 g, 19.58 mmol) was added to a solution of 3,5-diisopropyl-4-hydroxybenzaldehyde (4 g, 19.58 mmol) in tetrahydrofuran (40 ml) followed by addition of 2-hydroxyethylmorpholine (2.57 g, 19.58 mmol) and then the dropwise addition of diethylazodicarboxylate (3.41 g, 19.58 mmol). The mixture was stirred at room temperature for 12 hours. 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 (2×150ml), basified to pH 9 with solid sodium bicarbonate and extracted with ethyl acetate (3×150 ml). The organic layers were combined, dried over magnesium sulfate and concentrated to afford 900 mg (14%) of 3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde as a yellowish oil.

後処理

  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 (2×150ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0b39b6e87327452e9407713dc876b76e
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

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