Ammonium Chloride → 1-vinyl-13-oxabicyclo[10.1.0]tridecane

HRID 1061086Notes

Reaction equation

Cl[CH:2]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:14].[CH:15]([Mg]Cl)=[CH2:16].CN1C(=O)N(C)CCC1.[Cl-].[NH4+]>C1COCC1>[CH:15]([C:4]12[O:14][CH:3]1[CH2:2][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)=[CH2:16]

Participants

Conditions

Temperature: 50 °C

Procedure

A four-neck flask equipped with a thermometer, stirrer and condenser tube was charged with 100 g (0.46 mol) of 2-chlorocyclododecanone and 122 g of tetrahydrofuran, and at −10 to 0° C., a THF solution of vinylmagnesium chloride (0.82 mol) was added dropwise. The mixture was allowed to stand for reaction for 30 minutes, and 420 g (3.27 mol) of N,N′-dimethylpropyleneurea (DMPU) was added. The mixture was heated to 50° C. and allowed to stand for reaction for 1 hour, and saturated ammonium chloride aqueous solution was added dropwise for inactivation. The reaction mixture was subjected to extraction with hexane, and the solvent was recovered. The residue was distilled to obtain 1-vinyl-13-oxabicyclo[10.1.0]tridecane (80 g, 0.38 mol, chemical purity 98%, cis form:trans form=88:12). The yield was 82%.

Workup

customA four-neck flask equipped with a thermometer, stirrer and condenser tube
customto stand for reaction for 30 minutes
customto stand for reaction for 1 hour
extractionThe reaction mixture was subjected to extraction with hexane
customthe solvent was recovered
distillationThe residue was distilled

Sources & evidence

ORD record: ord-7a9a8a67641344f88f5dca5e0e08be22
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06525207B1

Reaction notes

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