1,1-Dibromoethane → 4-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol

HRID 1756015Notes

Reaction equation

HRID 1756015 reaction equation
[Mg].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=1.BrC(Br)C.[CH2:22]1[O:24][CH2:23]1.O1CCCC1>O1CCCC1.O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:22][CH2:23][OH:24])=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 112011,1-DibromoethaneHCID 5462224MagnesiumHCID 133067582-(4-bromophenethoxy)tetrahydro-2H-pyranHCID 21868110Ethylene oxide tetrahydrofuran

Product 1

HCID 542369074-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl alcoholYield 48.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Magnesium (1.31 g, 53.90 mmol) was added to a solution of 4-(2-(tetrahydropyran-2-yloxy)ethyl)bromobenzene (14.00 g, 49.09 mmol) in tetrahydrofuran (20 ml). Then dibromoethane (0.1 ml) was added under an atmosphere of nitrogen gas, and the mixture was stirred under room temperature for 1 hour. After cooling to ice-cooling temperature, 2M-ethylene oxide/tetrahydrofuran solution (49.09 ml, 98.18 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Then, water (40 ml) was added to the reaction mixture. The mixture was extracted with ethyl ether and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2) to give the desired 4-(2-(tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol (6.00 g, 42%).

Workup

  1. temperatureAfter cooling to ice-
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 2 hours
  4. extractionThe mixture was extracted with ethyl ether
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (=8/2)

Sources & evidence

ORD record
ord-792cb5ff81a8446bb4a470c2632fe0f4
Source dataset
uspto-grants-1995_08
Patent number
US05439911

Reaction notes

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