Sodium Chloride → HCID 68407169, compound

HRID 1176170Notes

Reaction equation

HRID 1176170 reaction equation
[CH2:1]([N:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=O)=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Na+].[Cl-].[CH2:24]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH2:24])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 8028Tetrahydrofuran2×HCID 11289255Benzaldehyde, 4-(dihexylamino)-

Product 1

HCID 68407169HCID 68407169, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Conditions

Temperature
0 °C

Procedure

To Methyltriphenylphosphonium bromide (3.07 g, 8.59×10−3 mol) in 50 ml of dry THF was added w-BuLi (2.2 M solution in hexane, 4.00 ml, 8.80×10−3 mol) dropwise at −78° C. After 2.5 h, the reaction mixture was gradually warmed up to 0° C., and again cooled to −78° C. N,N-dihexyl-4-formylaniline (2.26 g, 7.81×10−3 mol) in 15 ml of dry THF was slowly added to the reaction mixture. The reaction mixture was stirred overnight and meanwhile gradually warmed up to 10° C. Aqueous NaCl was added to the reaction mixture and the organic layer was extracted with petroleum ether. The organic layer was dried over Na2SO4. After the solvent was evaporated, the residue was chromatographed on silica gel with 1:1 hexane:CHCl3. Yield=0.775 g (35% based on 2.26 g of N,N-dihexyl-4-formylaniline). 1H NMR (250 MHz, CDCl3): δ 7.27 (d, 2H, J=8.8 Hz, Ph-H), 6.61 (dd, 1H, J=10.9, 17.8 Hz, vinyl-H), 6.58 (d, 2H, J=8.9 Hz, Ph-H), 5.49 (dd, 1H, J=1.1, 17.6 Hz, vinyl-H), 4.97 (dd, 1H, J=0.9, 10.8 Hz, vinyl-H), 3.25 (t, 4H, J=1.7 Hz, NCH2), 1.48-1.66 (m, 4H, NCH2CH2—), 1.20-1.42 (m, 12H, —CH2—), 0.89 (t, 6H, J=6.6 Hz, —CH3). CI MS m/z: 288.269 ((M+H)+) (calcd 288.269).

Workup

  1. temperatureagain cooled to −78° C
  2. temperaturemeanwhile gradually warmed up to 10° C
  3. extractionthe organic layer was extracted with petroleum ether
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customAfter the solvent was evaporated
  6. customthe residue was chromatographed on silica gel with 1:1 hexane

Sources & evidence

ORD record
ord-401bad7d546243d181f772604651ff25
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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