Dimethylformamide → 3-Dodecylthiophene-2-carbaldehyde

HRID 1509348Notes

Reaction equation

HRID 1509348 reaction equation
C([Li])CCC.Br[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].CN([CH:27]=[O:28])C.[NH4+].[Cl-]>>[CH2:12]([C:11]1[CH:10]=[CH:9][S:8][C:7]=1[CH:27]=[O:28])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 104268162-Bromo-3-DodecylthiopheneHCID 178418339Butyllithium

Product 1

HCID 201494313-Dodecylthiophene-2-carbaldehydeYield 87%

Procedure

A solution of n-Butyllithium (1.6M in hexanes, 8 mL, 12.67 mmol) was added dropwise at −78° C. under N2 to a stirred solution of 2-bromo-3-dodecylthiophene (10) (4 g, 12.07 mmol in 96 mL of ether). During the whole addition, the reaction temperature was kept at −78° C. At this temperature, DMF (1.4 mL, 18.11 mmol) was slowly added and the mixture was allowed to warm to room temperature. The mixture was poured into a 1 M aqueous solution of NH4Cl and extracted with CH2Cl2. The organic layer was washed with water, dried over Na2SO4, and evaporated under reduced pressure. The residue was passed through a short column (silica gel, hexane/ethylacetate, 9:1) to give a light yellow liquid compound 11 in 87% yield. 1H-NMR (DCM-d2, 400 MHz) ppm 0.88 (t, 3H, J=6.8 Hz) ppm 1.27 (m, 18H) ppm 1.67 (td, 2H, J=7.6 Hz, J=15.1 Hz) ppm 2.96 (t, 2H) ppm 7.04 (d, 1H, J=5.0 Hz) ppm 7.66 (d, 1H, J=5.0 Hz) ppm 10.04 (s, 1H).

Workup

  1. additionDuring the whole addition
  2. customwas kept at −78° C
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2257c29c787d4c14abcfe5db8a256cd4
Source dataset
uspto-grants-2015_12
Patent number
US09221944B2

Reaction notes

Loading…