Ethanol → Ethyl 6-[(4,4,5,5,5-pentafluoropentyl)oxy]hexanoate

HRID 459684Notes

Reaction equation

CC1C=CC(S([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])(=O)=O)=CC=1.[F:22][C:23]([F:32])([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:25][CH2:26]O.CC(C)([O-])C.[K+].C(O)C>O1CCCC1>[F:22][C:23]([F:32])([C:28]([F:31])([F:30])[F:29])[CH2:24][CH2:25][CH2:26][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

Conditions

Temperature: 200 °C

Procedure

To a stirred solution of the product of step (a) (500 mg) and 4,4,5,5,5-pentafluoropentan-1-ol (284 mg) in tetrahydrofuran (10 ml) was added potassium tert-butoxide (1M in tetrahydrofuran; 1.6 ml) and the reaction was stirred at 200° C. for 2 hours. An additional charge of potassium tert-butoxide (1M in tetrahydrofuran; 1.6 ml) was added and the reaction was stirred for a further 18 hours. Ethanol (5 ml) was added and the reaction was stirred for 30 mlnutes. The reaction mixture was partitioned between dichloromethane (300 ml) and water (300 ml). The organic layer was dried over magnesium sulphate and the solvent was removed in vacuo. Purification by column chromatography on silica gel (5 g Bond Elut cartridge) eluting with 20% ethyl acetate in cyclohexane gave the title compound as a clear oil (100 mg).

Workup

additionwas added
stirringthe reaction was stirred for a further 18 hours
stirringthe reaction was stirred for 30 mlnutes
customThe reaction mixture was partitioned between dichloromethane (300 ml) and water (300 ml)
dry with materialThe organic layer was dried over magnesium sulphate
customthe solvent was removed in vacuo
customPurification by column chromatography on silica gel (5 g Bond Elut cartridge)
washeluting with 20% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-5fc9b9c0de2443bb91b34f635e0d3e32
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07195752B2

Reaction notes

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