Tetrahydrofuran → 2-(4-bromophenethoxy)tetrahydro-2H-pyran

HRID 2305057Notes

Reaction equation

HRID 2305057 reaction equation
[Br:1][C:2]1(OCC)[CH:7]=[CH:6][C:5](O)=[CH:4][CH2:3]1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:30]1CC[CH2:32][CH2:31]1>O>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]1[O:30][CH2:31][CH2:32][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 673212194-Bromophenetyl alcohol

Product 1

HCID 133067582-(4-bromophenethoxy)tetrahydro-2H-pyranYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 15.67 g of 4-bromophenetyl alcohol, 6.88 g of 3,4-dihydro-2H-pyran, a catalytic amount of p-toluenesulfonic acid monohydrate, and 100 ml of tetrahydrofuran was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure, which afforded 21.5 g (yield, 97%) of 4-(2-(2-tetrahydropyranyloxy)ethyl)-1-bromobenzene, m.p., 93.9° C.

Workup

  1. extractionextracted twice with diethyl ether
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure, which

Sources & evidence

ORD record
ord-a394e319ff8c4ba78cd2c9df2342aa2f
Source dataset
uspto-grants-2002_08
Patent number
US06437184B1

Reaction notes

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