Triphenylphosphine → 3-Cyclohexyl-4-morpholinoethoxychlorobenzene

HRID 1860760Notes

Reaction equation

HRID 1860760 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-8e9068e78bac4804afbd664d0815b37d
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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