Tetrahydrofuran → HCID 67775099, compound

HRID 705904Notes

Reaction equation

HRID 705904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH3:17].[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:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[CH2:20])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH3:17]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 10705613HCID 10705613, compound

Product 1

HCID 67775099HCID 67775099, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

To a stirred suspension of 4-[(4-chloro-3-methylphenyl)oxy]benzaldehyde (4.2 g, 17.03 mmol) and methyl(triphenyl)phosphonium bromide (6 g, 16.80 mmol) in dry THF (50 mL) was added NaH (3.4 g, 85 mmol) under nitrogen at 0° C. 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 (2.46 g, 59% yield) as a light green oil. LCMS: rt=4.34 min, [M+H+]=280

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-72794cdedee2409ea1e35f9412984b88
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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