3,4-dihydro-2H-pyran → 1-Tetrahydropyranyloxy-1-(2-bromophenyl)prop-2-ene

HRID 1974764Notes

Reaction equation

HRID 1974764 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:11])[CH:9]=[CH2:10].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.O=P(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>O1CCCC1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:11][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH:9]=[CH2:10]

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 191022201-(2-Bromophenyl)prop-2-en-1-ol

Product 1

HCID 191022221-Tetrahydropyranyloxy-1-(2-bromophenyl)prop-2-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(2-bromophenyl)prop-2-en-1-ol) (31.0 g; 0.145 mol) in 150 ml of dry THF (tetrahydrofuran) was added 20 ml of 3,4-dihydro-2H-pyran and then 1 ml of POCl3 and the mixture stirred over the weekend at room temperature. The reaction mixture was neutralized with saturated NaHCO3 and concentrated down. The resulting material was partitioned between water and diethyl ether and the aqueous layer extracted again with diethyl ether. The organics were combined and washed with water and then brine and dried over K2CO3 and concentrated. The crude subtitle compound was chromatographed by HPLC using a solvent gradient from pure hexane to 5% ethyl acetate in hexane to afford the subtitle compound.

Workup

  1. concentrationconcentrated down
  2. customThe resulting material was partitioned between water and diethyl ether
  3. extractionthe aqueous layer extracted again with diethyl ether
  4. washwashed with water
  5. dry with materialbrine and dried over K2CO3
  6. concentrationconcentrated
  7. customThe crude subtitle compound was chromatographed by HPLC

Sources & evidence

ORD record
ord-0b50df0dce4347c7b836d650d1ccb2e6
Source dataset
uspto-grants-1994_02
Patent number
US05283361

Reaction notes

Loading…