Beta-Propiolactone → tetrahydro-3-(2-propenyl)-2H-pyran-2-one

HRID 1787406Notes

Reaction equation

[C:1]1(=[O:7])[O:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8](Br)[CH:9]=[CH2:10].C1(=O)OCC1.BrCCCCCCCCC=C>>[CH2:10]([CH:2]1[CH2:3][CH2:4][CH2:5][O:6][C:1]1=[O:7])[CH:9]=[CH2:8]

Participants

Reactant 4

HCID 2365Beta-Propiolactone

HCID 7841Allyl bromide

HCID 10953Delta-Valerolactone

HCID 54338410-Bromo-1-decene

Product 1

HCID 11263532tetrahydro-3-(2-propenyl)-2H-pyran-2-oneYield 70%

Procedure

9.81 g of tetrahydro-3-(2-propenyl)-2H-pyrane-2-one of interest were prepared in the same manner as in Preparation Example 2Z-3 except that 10.01 g (100.0 mmol) of δ-valerolactone and 14.52 g (110.0 mmol) of allyl bromide were used instead of β-propiolactone and 10-bromo-1-decene described in Preparation Example 2Z-3, respectively.

Sources & evidence

ORD record: ord-742de45adb86474ab21a2f02f9bda3fd
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07510813B2

Reaction notes

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