Acetic Anhydride → HCID 18319018, compound

HRID 1383954Notes

Reaction equation

[CH2:1]([S:13]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])=[CH:21][CH:20]=1)(=[O:15])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.[C:40](OC(=O)C)(=[O:42])[CH3:41]>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:1]([S:13]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]/[CH:26]=[C:27](\[O:32][C:40](=[O:42])[CH3:41])/[C:28]([F:29])([F:30])[F:31])=[CH:21][CH:20]=1)(=[O:14])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

Conditions

Temperature: -25 °C

Procedure

A solution of 4-[4-[2-(dodecylsulfonyl)ethoxy]phenyl]-1,1,1-trifluoro-2-butanone (1.10 g, 2.30 mmol) in dichloromethane (15 ml) was cooled to −25° C. and treated with triethylamine (0.5 ml) and 4-dimethylaminopyridine (0.560 g, 4.58 mmol). Then acetic anhydride (0.65 ml, 6.9 mmol) was added and the resulting mixture was stirred at −25° C. for 2.5 h. The solution was then diluted with ethyl acetate, washed with saturated sodium bicarbonate, dried (magnesium sulfate) and evaporated in vacuo. The residue was chromatographed on silica gel (elution toluene-ethyl acetate, 9:1) to give 0.94 g (78%) of a solid which was recrystallized from hexane to give white crystals: mp 48-49° C.

Workup

washwashed with saturated sodium bicarbonate
dry with materialdried (magnesium sulfate)
customevaporated in vacuo
customThe residue was chromatographed on silica gel (elution toluene-ethyl acetate, 9:1)

Sources & evidence

ORD record: ord-fc25a8b93cef4153b290286e10d7dc0d
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06255496B1

Reaction notes

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