4-Toluenesulfonyl chloride → HCID 57422600, compound

HRID 2426778Notes

Reaction equation

HRID 2426778 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:8])[CH2:7][CH2:6][CH2:5]1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>C1COCC1>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:1][CH2:2][CH2:3][C:4]2([OH:8])[CH2:7][CH2:6][CH2:5]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 129560861-(2-Hydroxyethyl)cyclobutanol

Product 1

HCID 57422600HCID 57422600, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an atmosphere of nitrogen, potassium tert-butoxide was added under ice-cooling to a mixture of cyclobutanone, ethyl chloroacetate and THF, spending 40 minutes, followed by stirring at 0° C. for 2 hours, raising the temperature to room temperature, and stirring at room temperature for 1 day, thereby obtaining ethyl 1-oxaspiro[2,3]hexane-2-carboxylate. A diethyl ether solution of the resulting ethyl 1-oxaspiro[2,3]hexane-2-carboxylate was added to a THF suspension of lithium aluminum hydride under ice-cooling in an atmosphere of nitrogen, followed by stirring at room temperature for 7 hours to obtain 1-(2-hydroxyethyl)cyclobutanol. A mixture of the resulting 1-(2-hydroxyethyl)cyclobutanol, 4-methylbenzenesulfonyl chloride, triethylamine and THF was stirred at room temperature for 16 hours to obtain 2-(1-hydroxycyclobutyl)ethyl 4-methylbenzenesulfonate.

Sources & evidence

ORD record
ord-0079b58822114a03acfba7c3cf01e73c
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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