Tetrahydrofuran → HCID 13767638, compound

HRID 2118546Notes

Reaction equation

HRID 2118546 reaction equation
C[O-:2].[Na+].C(N(CC)CC)C.[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20](Cl)(=[O:22])=[O:21])([O-:13])=[O:12].[O:24]1[CH2:28]C[CH2:26][CH2:25]1>>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([O:22][CH2:26][C@@H:25]1[O:24][CH2:28]1)(=[O:2])=[O:21])([O-:13])=[O:12]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 13767638HCID 13767638, compoundYield 46.6%

Procedure

14.90 g of the diol compound obtained in (A) above was dissolved in 150 ml of tetrahydrofuran, and with ice cooling, 6.49 g of sodium methoxide was added. The mixture was stirred for 2 hours. To the reaction mixture was added 27.8 ml of triethylamine, and a solution of 22.2 g of o-nitrobenzenesulfonyl chloride in 50 ml of tetrahydrofuran was added dropwise. The mixture was stirred overnight. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography [solvent: benzene-chloroform (2:1)] to give 7.31 g (yield 46.6%) of the desired compound as a pale yellow viscous oil.

Workup

  1. stirringThe mixture was stirred overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography [solvent: benzene-chloroform (2:1)]

Sources & evidence

ORD record
ord-358106e184db4dc78014961bb1ff8624
Source dataset
uspto-grants-1987_07
Patent number
US04678803

Reaction notes

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