Methyl vinyl ketone → HCID 21461384, compound

HRID 1941522Notes

Reaction equation

HRID 1941522 reaction equation
[Br:1][CH2:2][CH:3]1[O:12][CH2:11][CH:10]2[CH:6]([O:7][C:8]([CH3:14])([CH3:13])[O:9]2)[CH2:5][O:4]1.Br[CH2:16]C1OCC(O)C(O)CO1.CC(C=C)=O>>[Br:1][CH2:2][CH:3]1[O:12][CH2:11][CH:10]2[CH:6]([O:7][C:8]([CH3:14])([CH:13]=[CH2:16])[O:9]2)[CH2:5][O:4]1

Participants

4

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 21461382HCID 21461382, compoundHCID 21461387HCID 21461387, compound

Product 1

HCID 21461384HCID 21461384, compoundYield 54%

Procedure

4-Bromomethyl-9-methyl-9-vinyl-3,5,8,10-tetraoxabicyclo[5.3.0]decane was prepared in a similar way to 4-bromomethyl-9,9-dimethyl-3,5,8, 10-tetraoxabicyclo [5.3.0]decane starting from 220 mmol (50 g) of 2-bromomethyl-5,6-dihydroxy-1,3-dioxepane and from 1.36 mol (95.5 g) of methylvinyl ketone, fractional distillation giving 33.2 g of 4-bromomethyl-9-methyl-9-vinyl-3,5,8, 10-tetraoxabicyclo [5.3.0]decane (54% yield) with a boiling point from 94° to 101° C. (0.2 mbar).

Sources & evidence

ORD record
ord-4402bb48ada44b93b3713588b7ea1598
Source dataset
uspto-grants-1997_12
Patent number
US05703249

Reaction notes

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