Water → HCID 18401527, compound

HRID 1018477Notes

Reaction equation

HRID 1018477 reaction equation
[Br-].[OH:2][CH2:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH2:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[C:39]([CH3:42])[CH:40]=O)=[CH:34][CH:33]=1)[CH3:30].O>O1CCCC1.CCCCCC>[CH2:29]([O:31][C:32]1[CH:37]=[CH:36][C:35](/[CH:38]=[C:39](\[CH3:42])/[CH:40]=[CH:4]/[CH:3]=[O:2])=[CH:34][CH:33]=1)[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 2733550(2-Hydroxyethyl)triphenylphosphonium bromideHCID 54456843HCID 54456843, compoundHCID 178418339Butyllithium

Product 1

HCID 18401527HCID 18401527, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a stirred suspension of 2-hydroxyethyltriphenylphosphonium bromide (30 g, 0.077 mol) in dried tetrahydrofuran (300 ml) cooled to −40° C. under an atmosphere of nitrogen was added a solution of n-butyllithium in hexane (2.5M, 58.5 ml) dropwise. The resulting orange suspension was then stirred at 50° C. with occasional ultrasonication for 3 h, cooled to −60° C. and a solution of 3-(4-ethoxyphenyl)-2-methylpropenaldehyde (7.4 g, 0.039 ml) in dried tetrahydrofuran (25 ml) added dropwise and allowed to warm to 0° C. After ½ h, water was added and the organic phase separated. The aqueous phase was extracted with diethyl ether and the combined organic phases washed four times with water and then brine. The organic phase was dried over magnesium sulphate, filtered and evaporated to an oil. The oil was dissolved in a minimum of diethyl ether and chromatographed on flash silica eluting with hexane then hexane-diethyl ether (3:2) to give 5-(4-ethoxyphenyl)-4-methylpent-2E,4E-dienal as a white solid.

Workup

  1. temperaturecooled to −60° C.
  2. temperatureto warm to 0° C
  3. waitAfter ½ h
  4. customthe organic phase separated
  5. extractionThe aqueous phase was extracted with diethyl ether
  6. washthe combined organic phases washed four times with water
  7. dry with materialThe organic phase was dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated to an oil
  10. dissolutionThe oil was dissolved in a minimum of diethyl ether
  11. customchromatographed on flash silica eluting with hexane

Sources & evidence

ORD record
ord-c76a4a8c5a004ad3b13962eaf2c1d581
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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