2-Methoxypropene → HCID 10592560, compound

HRID 1075479Notes

Reaction equation

HRID 1075479 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[OH:18][C@@H:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:20][C:21]([O:23][CH3:24])=[O:22].[CH3:36][O:37][C:38]([CH3:40])=[CH2:39]>C(OCC)C>[CH3:36][O:37][C:38]([O:18][C@@H:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:20][C:21]([O:23][CH3:24])=[O:22])([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 83002-MethoxypropeneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 11021563(S)-Methyl 3-hydroxytetradecanoate

Product 1

HCID 10592560HCID 10592560, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyridinium p-toluenesulfonate (90 mg) was added to a solution of methyl (S)-3-hydroxytetradecanoate (VIII, 10.32 g, 40 mmol) in 2-methoxypropen (40 mL). After stirring for 20 min at room temperature the reaction mixture was diluted with diethyl ether (30 mL) and extracted first with a saturated aqueous solution of sodium hydrogen carbonate (3 mL) and then with water (2×2 mL). The combined organic phases were dried (Na2SO4) and concentrated under reduced pressure. The residual colorless oil (13.20 g, 99%) was used in the next step without further purification. [α]25D +10.01 (c=0.5 in hexane); 1H NMR (DMSO-D6) δ 0.86 (t, J=7 Hz, 3H), 1.24-1.27 (m, 26H), 1.44-1.46 (m, 2H), 3.09 (s, 3H), 3.58 (s, 3H), 4.03-4.05 (m, 1H); 13C NMR (DMSO-D6) δ 13.85, 22.02, 22.05, 24.26, 24.86, 28.67, 28.91, 28.97, 28.98, 29.03, 30.93, 31.27, 35.13, 40.21, 48.46, 51.15, 67.67, 100.35, 171.62. Anal. Calcd for C19H38O4 : C, 69.05; H, 11.59. Found: C, 69.00; H, 11.63.

Workup

  1. extractionextracted first with a saturated aqueous solution of sodium hydrogen carbonate (3 mL)
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residual colorless oil (13.20 g, 99%) was used in the next step without further purification

Sources & evidence

ORD record
ord-6ee40d0579e04cefa3581d0c3bdd551d
Source dataset
uspto-grants-1999_05
Patent number
US05902886

Reaction notes

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