Tetrahydrofuran → HCID 67776066, compound

HRID 705902Notes

Reaction equation

HRID 705902 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[H-].[Na+].[CH2:20]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[CH2:20])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86018147HCID 86018147, compound

Product 1

HCID 67776066HCID 67776066, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 4-[(3-chloro-4-methylphenyl)oxy]benzaldehyde (5.5 g, 22.30 mmol) and methyl(triphenyl)phosphonium bromide (7.96 g, 22.30 mmol) in THF (50 mL) was added NaH (3.12 g, 78 mmol) under nitrogen at 0° C. After the mixture was stirred at room temperature for 3 h, the organic layer was washed three times with brine, dried over Na2SO4, filtered, and concentrated. Purification via flash chromatography afforded the title compound (2.8 g, 51.3% yield). LCMS: rt=4.37 min, [M+H+]=323

Workup

  1. washthe organic layer was washed three times with brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification via flash chromatography

Sources & evidence

ORD record
ord-d4f27544662a4305bc31cd378f0a2944
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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