1-Phenyl-1-propanol → (+/-)-3-(2,4-Dichloro-phenyl)-2,6-dimethyl-7-(1-phenyl-propoxy)-pyrazolo[5,1-b]oxazole

HRID 1671297Notes

Reaction equation

HRID 1671297 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C(N(CC)CC)C.[C:39]1([CH:45]([OH:48])[CH2:46][CH3:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:51]=1[C:57]1[N:58]2[N:65]=[C:64]([CH3:66])[C:63](O)=[C:59]2[O:60][C:61]=1[CH3:62].[Cl-].[NH4+]>C1COCC1>[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:51]=1[C:57]1[N:58]2[N:65]=[C:64]([CH3:66])[C:63]([O:48][CH:45]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:46][CH3:47])=[C:59]2[O:60][C:61]=1[CH3:62]

Participants

8

Reactant 6

HCID 71471-Phenyl-1-propanolHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 5462977Diethyl azodicarboxylateHCID 591861133-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-ol

Product 1

HCID 59186134(+/-)-3-(2,4-Dichloro-phenyl)-2,6-dimethyl-7-(1-phenyl-propoxy)-pyrazolo[5,1-b]oxazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of triphenylphosphine (66.2 mg, 0.252 mmol) in THF (1.683 ml) under N2 at RT is added DEAD (0.040 ml, 0.252 mmol) followed by triethylamine (0.035 ml, 0.252 mmol), 1-phenyl-1-propanol (0.035 ml, 0.252 mmol) and 3-(2,4-dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-ol (Intermediate IC) (50 mg, 0.168 mmol). The reaction mixture is stirred overnight and then added to sat. ammonium chloride (50 ml). The mixture is extracted with EtOAc (60 ml) and the combined organic phases are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by ISCO combiflash chromatography, eluting with 0 to 100% (iso-hexane/EtOAc) on a 12 g SiO2-column to give the title compound as a solid; MS: m/z 415.21 [M+H]+; 1H NMR (400 MHz, CDCl3) δ 7.52 (2H, m), 7.35 (6H, m), 4.58 (1H, t), 2.25 (3H, s), 2.20 (3H, s), 2.15 (1H, m), 1.94 (1H, m), 1.05 (3H, t).

Workup

  1. extractionThe mixture is extracted with EtOAc (60 ml)
  2. washthe combined organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by ISCO combiflash chromatography
  6. washeluting with 0 to 100% (iso-hexane/EtOAc) on a 12 g SiO2-column

Sources & evidence

ORD record
ord-77d15ba550854eacb32ab7e3f58b77ab
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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