Sodium Chloride → HCID 12967236, compound

HRID 1610043Notes

Reaction equation

HRID 1610043 reaction equation
[C:1]([C:5]1([OH:20])[C:9]([CH3:11])([CH3:10])[CH2:8][O:7][CH:6]1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.C1C(=O)N([Br:33])C(=O)C1.[Cl-].[Na+]>O>[Br:33][C:15]1[CH:16]=[CH:17][C:12]([CH:6]2[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([OH:20])[C:9]([CH3:11])([CH3:10])[CH2:8][O:7]2)=[CH:13][C:14]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 67184N-bromobutanimide2×HCID 12967235HCID 12967235, compound2×

Product 1

HCID 12967236HCID 12967236, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

2.16 g (7.77 mmol) of 3-t-butyl-3-hydroxy-2-(3-methoxyphenyl)-4,4-dimethyl-2,3,4,5-tetrahydrofuran (compound (5)) was added to a mixed solvent of 20 ml of THF and 2 ml of H2O, followed by stirring at 0° C. To this solution, 1.54 g (8.65 mmol) of NBS was added, and while gradually raising the temperature to room temperature, stirring was continued overnight. Then, 140 mg (0.787 mmol) of NBS was further added, followed by stirring for 6 hours. The reaction mixture was put into a saturated sodium chloride aqueous solution and extracted with ethyl acetate. The extract layer was washed sequentially with an aqueous sodium thiosulfate solution and a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrated product was crystallized from a mixed solvent of ethyl acetate and hexane to obtain 1.323 g of 2-(4-bromo-3-methoxyphenyl)-3-t-butyl-3-hydroxy-4,4-dimethyl-2,3,4,5-tetrahydrofuran (compound (6)) in a yield of 47.7%.

Workup

  1. temperaturewhile gradually raising the temperature to room temperature
  2. stirringstirring
  3. stirringby stirring for 6 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract layer was washed sequentially with an aqueous sodium thiosulfate solution
  6. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrated product was crystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-70e70c597ba64735a6d8c278d39f58a3
Source dataset
uspto-grants-2006_01
Patent number
US06982336B2

Reaction notes

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