Allyl bromide → HCID 18461547, compound

HRID 2303451Notes

Reaction equation

HRID 2303451 reaction equation
[O:1]1[C:5](=[O:6])[CH2:4][CH:3]2[CH2:7][CH2:8][CH2:9][CH:2]12.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:20](Br)[CH:21]=[CH2:22]>C1COCC1>[CH2:22]([CH:4]1[C:5](=[O:6])[O:1][CH:2]2[CH2:9][CH2:8][CH2:7][CH:3]12)[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 11665410hexahydro-cyclopenta[b]furan-2-one

Product 1

HCID 18461547HCID 18461547, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Analogously to the procedure of Example 1, the title compound is was prepared from 1.2 g (9.5 nmuol) of hexahydro-cyclopenta[b]furan-2-one, 10 ml of 1 molar lithium bis-(trimethylsilyl)-amide solution in THF and 1.29 g (9.5 mmol) of allyl bromide in 20 ml of THF. Yield: 1.25 g (79%) of a colourless oil. 1H-NMR(200 MHz; [d6]-DMSO): δ[ppm]: 1.47-1.89 (br m,6H), 2.15-2.55 (br m,4H), 4.41 (m,1H), 5.12 (dd,1H), 5.18 (dd,1H), 5.76 (ddt,1H)

Sources & evidence

ORD record
ord-dc5ebddfb923426c8b77fcefa126918e
Source dataset
uspto-grants-2002_08
Patent number
US06433004B1

Reaction notes

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