Tetrahydrofuran → HCID 86660539, compound

HRID 2193831Notes

Reaction equation

HRID 2193831 reaction equation
C([N:3]([CH2:6]C)CC)C.[SH:8]C1C=CC=CN=1.[C:15](Cl)(=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25].[CH2:28]1[CH2:32]O[CH2:30][CH2:29]1>>[C:15](=[S:8])([O:26][C:6]1[CH:32]=[CH:28][CH:29]=[CH:30][N:3]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 3804210-Undecenoyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 86660539HCID 86660539, compound

Procedure

A solution of triethylamine (2.5 mL), THF (20 mL) and 2-mercaptopyridine (0.77 g, 6.95 mmol) was stirred for 15 minutes at 0° C. A solution of undec-10-enoyl chloride (X) (1.17 g, 5.79 mmol) in THF (20 mL) was added all at once. Immediately the reaction was then quenched by adding an aqueous HCl-solution (2.0 M, 50 mL) at 0° C. and subsequently extracted with diethyl ether. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a yellow oil. The crude green oil was purified by column chromatography using silica gel (eluent CH2Cl2). The compound (XI) was obtained as a lightly yellow oil. (0.64 g, 40%). 1H-NMR (CDCl3): δ=8.60-8.55 (m, 1H), 7.73-7.65 (m, 1H), 7.60-7.54 (m, 1H), 7.27-7.20 (m, 1H), 5.84-5.68 (m, 1H), 5.01-4.84 (m, 2H), 2.65 (t, J=7.5 Hz, 2H), 1.99 (q, J=13.7 Hz, J=6.7 Hz, 2H), 1.73-1.61 (m, 2H), 1.40-1.17 (m; 10H).

Workup

  1. customImmediately the reaction was then quenched
  2. additionby adding an aqueous HCl-solution (2.0 M, 50 mL) at 0° C.
  3. extractionsubsequently extracted with diethyl ether
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with diethylether
  6. washThe combined organic phases were washed with a saturated bicarbonate solution and brine
  7. dry with materialdried over MgSO4
  8. customevaporated under reduced pressure
  9. customto give a yellow oil
  10. customThe crude green oil was purified by column chromatography

Sources & evidence

ORD record
ord-55db1d78f7a843a9b6d104ca4ce575e0
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

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