Sodium hydride → HCID 67050488, compound

HRID 2194740Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11](=[O:23])[CH2:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:24][C:25]([F:36])([F:35])[CH2:26]OS(C(F)(F)F)(=O)=O>C1COCC1>[CH2:16]([O:15][C:13](=[O:14])[CH:12]([CH2:26][C:25]([F:36])([F:35])[F:24])[C:11]([O:10][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 60% sodium hydride (0.678 g, 16.97 mmol) in THF (100 mL) at room temperature was added malonic acid dibenzyl ester (4.825 g, 16.97 mmol) to give a clear solution after 30 min. Trifluoro-methanesulfonic acid 2,2,2-trifluoro-ethyl ester (3.52 g, 15.43 mmol) was added and reaction mixture was stirred at 50° C. for 48 h. The reaction mixture was concentrated, partioned between ethyl ether and washed with saturated ammonium chloride solution and acidified with 1N HCl. The mixture was extracted with ethyl ether (2×), dried (MgSO4), and concentrated. The resulting residue was purified by flash column chromatography (silica gel, 0 to 0% ethyl ether/hexanes) to give a colorless oil (3.844 g, 68%). 1H NMR (300 MHz, CDCl3): δ 7.4-7.2 (m, 10H), 5.15 (s, 4H), 3.75 (t, J=6.9 Hz, 1H), 2.9-7.7 (m, 2H).

Workup

customto give a clear solution after 30 min
customreaction mixture
concentrationThe reaction mixture was concentrated
washwashed with saturated ammonium chloride solution
extractionThe mixture was extracted with ethyl ether (2×)
dry with materialdried (MgSO4)
concentrationconcentrated
customThe resulting residue was purified by flash column chromatography (silica gel, 0 to 0% ethyl ether/hexanes)

Sources & evidence

ORD record: ord-292d7016cbf04211ab1d980b67dc5fe0
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334295B2

Reaction notes

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