3,4-dihydro-2H-pyran → 2-[(3-Bromophenyl)methoxy]oxane

HRID 341985

Reaction equation

HRID 341985 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[CH:6][CH:7]=1.[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][O:9][CH:11]2[CH2:12][CH2:13][CH2:14][CH2:15][O:10]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 80811Triphenylphosphonium bromideHCID 851413-Bromobenzyl alcohol

Product 1

HCID 152820642-[(3-Bromophenyl)methoxy]oxane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The alcohol of Step 1 (41.23 mmol), dihydropyran (12.5 mL, 137 mmol) and triphenylphosphine hydrobromide (725 mg, 2.11 mmol) were mixed together in 200 mL of CH2Cl2 and stirred for 2 days. The solvent was then evaporated and the title product was purified by flash chromatography on silica using EtOAc:toluene.

Workup

  1. customThe solvent was then evaporated
  2. customthe title product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-26550fcdd4ce4475a6345906644a73e3
Source dataset
uspto-grants-1999_01
Patent number
US05856322

Linked notes

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