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

HRID 24408

反応式

HRID 24408 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

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 (2×150 ml)
  4. extractionextracted with ethyl acetate (3×150 ml)
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-b74638abcaa1446e966896a2dd908b5f
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

関連ノート

読み込み中…