Ethyl Acetate → (3,3-Dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylethynyl)-trimethyl-silane

HRID 2373440Notes

Reaction equation

I[C:2]1[CH:14]=[CH:13][C:5]2[O:6][CH2:7][C:8]([CH3:12])([CH3:11])[CH2:9][O:10][C:4]=2[CH:3]=1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].CCOC(C)=O.O=[Si]=O>C(NC(C)C)(C)C.C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:11][C:8]1([CH3:12])[CH2:7][O:6][C:5]2[CH:13]=[CH:14][C:2]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:3][C:4]=2[O:10][CH2:9]1

Participants

Conditions

Temperature: 57 °C

Procedure

To a mixture of [PdCl2(PPh3)2] (1.73 g) and copper(I) iodide (845 mg) under Ar is added a degassed solution of 7-iodo-3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepine (7) (15.0 g) in diisopropylamine (225 ml) and THF (225 ml). Trimetylsilylacetylene (7.27 g) is added and the mixture is stirred over night at 57° C. After addition of AcOEt (1 L) and filtration over dicalite, the solution is washed with 1 N aq. HCl sol. (3×1 L) and brine (2×1 L). The organic layer is dried over Na2SO4 and the solvent is evaporated to yield (3,3-dimethyl-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-ylethynyl)-trimethyl-silane (6b) as a brown oil.

Workup

washthe solution is washed with 1 N aq. HCl sol. (3×1 L) and brine (2×1 L)
dry with materialThe organic layer is dried over Na2SO4
customthe solvent is evaporated

Sources & evidence

ORD record: ord-d312b09f768c4ec68baffca2a05e9d02
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459480B2

Reaction notes

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