Triphenylphosphine → 3-Cyclohexyl-4-morpholinoethoxychlorobenzene

HRID 24361

Reaction equation

HRID 24361 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 542202543-Cyclohexyl-4-morpholinoethoxychlorobenzeneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-0587300284a0486c8710401c67d8f9c2
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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