3-Dodecylthiophene-2-carbaldehyde → HCID 58517367, compound

HRID 1509349Notes

Reaction equation

HRID 1509349 reaction equation
[CH2:1]([C:13]1[CH:17]=[CH:16][S:15][C:14]=1[CH:18]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>C1COCC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[CH2:1]([C:13]1[CH:17]=[CH:16][S:15][C:14]=1/[CH:18]=[CH:18]/[C:14]1[S:15][CH:16]=[CH:17][C:13]=1[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 1

HCID 201494313-Dodecylthiophene-2-carbaldehyde

Product 1

HCID 58517367HCID 58517367, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of low-valent Ti prepared from TiCl4 (0.94 mL, 8.56 mmol) and Zn (1.12 g, 17.11 mmol) in 42 mL of dry THF under N2 at 0° C. was added a dry solution of 11 (2 g, 7.13 mmol) in 14 mL of dry THF. After 2 h of refluxing, the mixture was cooled to room temperature, filtered to remove excess Zn, evaporated, poured into water and extracted with CH2Cl2. The organic phase was washed with water and dried over MgSO4. After solvent removal, the crude solid was purified by column chromatography (silica gel, hexane) to give a pale yellow solid compound 12 in 75% yield. 1H-NMR (CDCl3, 400 MHz) ppm 0.88 (t, 6H, J=6.8 Hz) ppm 1.31 (m, 36H) ppm 1.59 (td, 4H, J=7.4 Hz, J=14.7 Hz) ppm 2.65 (m, 4H) ppm 6.84 (d, 2H, J=5.2 Hz) ppm 6.99 (s, 2H) ppm 7.07 (d, 2H, J=5.2 Hz).

Workup

  1. additionTo a suspension of low-valent Ti
  2. temperatureAfter 2 h of refluxing
  3. filtrationfiltered
  4. customto remove excess Zn
  5. customevaporated
  6. additionpoured into water
  7. extractionextracted with CH2Cl2
  8. washThe organic phase was washed with water
  9. dry with materialdried over MgSO4
  10. customAfter solvent removal
  11. customthe crude solid was purified by column chromatography (silica gel, hexane)

Sources & evidence

ORD record
ord-ef404690717e48fabac5f2f8a8247bb5
Source dataset
uspto-grants-2015_12
Patent number
US09221944B2

Reaction notes

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