Diethyl Ether → HCID 54382316, compound

HRID 428313Notes

Reaction equation

P(=O)(O)O.C([CH:7](CC)[C:8]([N:10]([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12])=[O:9])C.[H-].[Na+].[F:21][C:22]([F:38])([F:37])[C:23]1[CH:36]=[CH:35][CH:34]=[CH:33][C:24]=1[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=O.C(OCC)C>C1COCC1.O>[CH:11]([N:10]([CH:14]([CH3:16])[CH3:15])[C:8](=[O:9])[CH:7]=[C:25]([C:24]1[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=1[C:22]([F:38])([F:37])[F:21])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of diethyl N,N-diisopropylacetamide phosphonate (8.4 g, 30 mmol) in THF (20 mL) was added dropwise to sodium hydride (80%, 0.85 g, 29 mmol) during 30 min, keeping the temperature below 30° C. A solution of 2-trifluoromethyl-benzophenone (5.0 g, 20 mmol) in THF (20 mL) was added and the reaction mixture was heated to 50° C. and kept at that temperature for 16 h. A second portion of the phosphorous ylide (15 mmol), prepared as above, was added. After another 24 h at 50° C. the mixture was partioned between diethyl ether and water. The etheral layer was evaporated and the residue chromatographed on silica (toluene-ethyl acetate 9:1) yielding 3.0 g (41%) as a mixture of the E- and Z-isomers. Labels a and b refer to the different isomers. 1H NMR (CDCl3-d) δ0.80 (d, 6Ha), 1.08 (d, 3Hb), 1.24 (t, 6Hb), 1.31 (d, 3Hb), 1.44 (d, 6Ha), 3.32 (m, 1Ha), 3.34 (m, 1Hb), 4.19 (m, 1Hb), 4.32 (m, 1Ha), 6.04 (s, 1Ha), 6.65 (s, 1Hb) and 7.18-7.75 (m, 9Ha, 9Hb).

Workup

customthe temperature below 30° C
additionwas added
customThe etheral layer was evaporated
customthe residue chromatographed on silica (toluene-ethyl acetate 9:1)
customyielding 3.0 g (41%)
additionas a mixture of the E- and Z-isomers

Sources & evidence

ORD record: ord-689f831f9bc54576ab163f90b68de987
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313132B1

Reaction notes

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