Triphenylphosphine → 3-Cyclohexyl-4-morpholinoethoxychlorobenzene

HRID 24361

反応式

HRID 24361 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:20]1([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[OH:33])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O[CH2:35][CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[CH:20]1([C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[O:33][CH2:35][CH2:36][N:37]2[CH2:42][CH2:41][O:40][CH2:39][CH2:38]2)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 831204-Chloro-2-cyclohexylphenolHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 542202543-Cyclohexyl-4-morpholinoethoxychlorobenzene収率 95%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triphenylphosphine (7.47 g, 19.58 mmol) was added to a solution of 2-cyclohexyl-4-chlorophenol (6 g, 28.48 mmol) and 2-hydroxyethylmorpholine (3.5 g, 28.48 mmol) in tetrahydrofuran (50 ml), followed by the dropwise addition of diethylazodicarboxylate (4.5 ml, 28.48 mmol). The mixture stirred at room temperature for 12 hours. The reaction mixture was concentrated under reduced pressure and triturated with dichloromethane/hexanes and then washed with more hexanes. Chromatography (silica, 10-20-30% ethyl acetate/hexanes) afforded 8.4 g (95%) of 3-cyclohexyl-4-morpholinoethoxy-chlorobenzene as a yellowish oil.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customtriturated with dichloromethane/hexanes
  3. washwashed with more hexanes

出典と根拠

ORDレコード
ord-0587300284a0486c8710401c67d8f9c2
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

関連ノート

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