Dimethylformamide → HCID 86676971, compound

HRID 574748Notes

Reaction equation

HRID 574748 reaction equation
[H-].[Na+].C[C:4]1([CH3:11])[O:8][CH:7]([CH2:9][OH:10])C[O:5]1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].CN(C)[CH:31]=[O:32]>>[C:4]([O:8][CH:7]([CH2:31][OH:32])[CH2:9][O:10][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])(=[O:5])/[CH:11]=[CH:28]\[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=[CH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 4

HCID 6228Dimethylformamide3×HCID 7528SolketalHCID 82131-BromohexadecaneHCID 24758Sodium hydride

Product 1

HCID 86676971HCID 86676971, compoundYield 57%

Procedure

To NaH (1.85 g, 60% dispersed in mineral oil) under argon was added anhydrous N, N-dimethylformamide (DMF, 30 mL) at RT. Solketal (2.20 g, 16.7 mmol) in 10 mL anhydrous DMF was then added dropwise with constant stirring. 1-Bromohexadecane (5.10 g, 16.7 mmol), dissolved in anhydrous DMF (20 mL) was then added to the reaction mixture dropwise and stirred for 72 hours. The reaction was quenched by adding about 5 mL of methanol. It was then poured into cold ice water (100 mL) and extracted with hexane (100 mL, 3×). The solvent was removed under reduced pressure and the residue chromatographed on silica gel using hexane-dichloromethane to obtain 1a (3.363 g, 57% yield); 1H NMR (in CDCl3): δ in ppm 0.83-0.86 (3H, t, J=6.5 Hz), 1.22 (26H, m), 1.33 (3H, s), 1.39 (3H, s), 1.52-1.55 (2H, m), 3.37-3.48 (4H, m), 3.68-3.71 (1H, t, J=6.5 Hz), 4.01-4.03 (1H, t, J=6.5 Hz), 4.20-4.25 (1H, quintet, J=6.0 Hz); 13C NMR (in CDCl3): 8 in ppm 14.3, 22.9, 25.6, 26.2, 27.0, 29.6, 29.7, 29.8, 29.9, 32.1, 67.1, 72.0, 72.1, 74.9, 109.5.

Workup

  1. additionwas then added to the reaction mixture dropwise
  2. customThe reaction was quenched
  3. additionby adding about 5 mL of methanol
  4. additionIt was then poured into cold ice water (100 mL)
  5. extractionextracted with hexane (100 mL, 3×)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-40c40e4335dd4cb39e53d2ad01d0611a
Source dataset
uspto-grants-2015_05
Patent number
US09034923B2

Reaction notes

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