Tetrahydrofuran → HCID 131712931, compound

HRID 1380475Notes

Reaction equation

HRID 1380475 reaction equation
[Li+:1].[C:2]1([S:8]([O-:11])(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li:16])CCC.[C:17]1(=[O:22])[CH2:21][CH2:20][CH2:19][CH2:18]1.C1COCC1>>[Li+:16].[Li+:1].[OH:22][C:17]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[S:8]([O-:11])(=[O:10])=[O:9])[CH2:21][CH2:20][CH2:19][CH2:18]1.[OH:22][C:17]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[S:8]([O-:11])(=[O:10])=[O:9])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8452CyclopentanoneHCID 19205774HCID 19205774, compoundHCID 178418339Butyllithium

Product 1

HCID 131712931HCID 131712931, compoundYield 80,169.398%

Procedure

A mixture of benzenesulfonic acid lithium salt (32.8 g, 0.20 mmol) and 500 ml THF was stirred in an ice bath while 138 ml (0.22 mol) of n-butyllithium solution (1.6M in hexane) was added. After stirring at room temperature for 1 hour the mixture was recooled to 0° and cyclopentanone (16.8 g, 0.20 mmol) was added dropwise; the reaction mixture was allowed to warm to ambient temperature and stirred for 24 hours. The precipitated product was collected by filtration and dried in a vacuum oven to yield 39.8 g of 2-(1-hydroxycyclopent-1-yl)benzenesulfonic acid dilithium salt.

Workup

  1. additionwas added
  2. customwas recooled to 0°
  3. temperatureto warm to ambient temperature
  4. stirringstirred for 24 hours
  5. filtrationThe precipitated product was collected by filtration
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-2f7e9032a60a4679b8675009b5ae2556
Source dataset
uspto-grants-1986_04
Patent number
US04582525

Reaction notes

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