Water → 2-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 574059

Reaction equation

HRID 574059 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:4][CH:3]=1.[Li]CCCC.[OH:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][CH:34]=1)[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].O>C1COCC1.CCCCCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][CH2:10][C:11]([CH3:14])([CH3:13])[N:12]=2)=[CH:6][CH:7]=1.[CH3:13][C:11]1([CH3:14])[CH2:10][O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:24]([OH:25])([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:23]3[CH:22]=[C:21]([OH:20])[CH:34]=[CH:33][CH:32]=3)=[CH:3][CH:4]=2)=[N:12]1

Participants

8

Reactant 4

HCID 962WaterHCID 830503-HydroxybenzophenoneHCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 178418339Butyllithium

Product 2

HCID 4033952-(4-Bromophenyl)-4,4-dimethyl-4,5-dihydrooxazoleHCID 599879993-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2-(4-Bromophenyl)-4,4-dimethyl-1,3-oxazoline 1 was prepared as described in Example 4. To a stirred solution of 2-(4-bromophenyl)-4,4-dimethyl-1,3-oxazoline (1.5 g, 6 mM) in anhydrous THF (10 mL) at −78° C. was added slowly n-BuLi (384 mg, 6 mM) in hexane over the period of 20 min. After that the reaction mixture was stirred at −78° C. for another 30 min. To this stirred solution was added 3-hydroxybenzophenone (534 mg, 2.7 mM) dissolved in anhy. THF (10 mL) by dropwise at −78° C. and allowed to stir at room temperature overnight. To this reaction mixture was added 20 mL of water to quench the reaction and extracted with CH2Cl2 (3×50 mL) and the combined extract was dried over anhydrous Mg2SO4. The oily residue obtained on evaporation of the solvent was purified by silica gel column chromatography using hexane/EtOAc (1:1) mixture gave 3-{[4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-phenyl]-hydroxy-phenyl-methyl}-phenol (2) as colorless crystalline solid. Yield: 0.855 g (85%). Mass: 374 (MH+), 372 (M-H).

Workup

  1. dissolutiondissolved in anhy
  2. customdropwise at −78° C.
  3. stirringto stir at room temperature overnight
  4. customto quench
  5. customthe reaction
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. extractionthe combined extract
  8. dry with materialwas dried over anhydrous Mg2SO4
  9. customThe oily residue obtained on evaporation of the solvent
  10. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fed17c506bf24ee89111b30b5c4683f4
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Linked notes

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