Acetic Anhydride → HCID 18319018, compound

HRID 1700942Notes

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-ac9fda0e2b7a443898def5a96cb9259d
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350892B1

Reaction notes

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