Tetrahydrofuran → HCID 15020144, compound

HRID 1898781Notes

Reaction equation

HRID 1898781 reaction equation
[H-].[Na+].C(OCCCCC[SH:11])C.I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1>CCCCCC>[C:20]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][S:11][CH2:26][CH2:27][O:28][CH2:29][CH3:25]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 15024840Ethyl 8-iodooctanoateHCID 23372466HCID 23372466, compound

Product 1

HCID 15020144HCID 15020144, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

NaH (0.39g, 9.6 mmol) was washed with hexane and then suspended in dry THF (45 mL). 5-Ethoxypentane-1thiol (8.7 mmol) in THF (8 mL) was added and stirred for 1 h at room temperature. Ethyl 8-iodooctanoate (2.4 g, 8.7 mmol) in THF (7 mL) was added and the mixture was refluxed for 6 h. After evaporation of the solvent, the residue was taken into ethyl acetate (150 mL). The organic phase was washed with water (2×50 mL), brine (50 mL), and dried (Na2SO4). The crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation to give the title compound, ethyl 9-thia-12-oxatetradecanoate; yield 52%; bp 118°-120° C./0.15 torr; NMR: 1.2 (3H, t, J=7 Hz), 1.25 (3H, t, J=7 Hz), 1.2-1.8 (10 H, m), 2.28 (2H, t, J=6.5 Hz), 2.55 (2H, t, J=7 Hz), 2.67 (2H, t, J=7 Hz), 3.44 (2H, t, J=7 Hz), 3.66 (2H, t, J=7 Hz), and 4.1 ppm (2H, q, J=7 Hz).

Workup

  1. temperaturethe mixture was refluxed for 6 h
  2. customAfter evaporation of the solvent
  3. washThe organic phase was washed with water (2×50 mL), brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. distillationThe crude product was purified by column chromatography on silica gel with ethyl acetate:hexane (1:5) and subsequent Kugelrohr distillation

Sources & evidence

ORD record
ord-4342701914b1480e970d12992589fa08
Source dataset
uspto-grants-1996_11
Patent number
US05571689

Reaction notes

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