HCID 22450238, compound → HCID 54517415, compound

HRID 2187092Notes

Reaction equation

[Cl-].[CH3:2][O:3][CH:4]=C1C=CC=CC1[PH+](C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:36][C:37]1[CH:50]=[CH:49][CH:48]=[CH:47][C:38]=1[C:39]([C:41]1[O:46][CH2:45][CH2:44][O:43][N:42]=1)=O>O1CCCC1>[O:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]1[O:36][C:37]1[CH:50]=[CH:49][CH:48]=[CH:47][C:38]=1[C:39]([C:41]1[O:46][CH2:45][CH2:44][O:43][N:42]=1)=[CH:2][O:3][CH3:4]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 31.2 g (0.091 mol) of methoxymethylene-triphenyl-phosphonium chloride and 10.2 g (0.091 mol) of potassium tert-butoxide in 100 ml of tetrahydrofuran is stirred for 20 minutes at 20° C. A solution of 13.3 g (0.0457 mol) of 3-[2-(tetrahydropyran-2-yloxy)-benzoyl]-5,6-dihydro-1,4,2-dioxazine in 100 ml of tetrahydrofuran is then added, and the mixture is refluxed at the boil for 12 hours. The mixture is concentrated under reduced pressure and the residue is partitioned between water and ethyl acetate. The organic phase is separated off and dried over sodium sulphate. The residue is chromatographed on silica gel using cyclohexane/ethyl acetate (1:1). 9.2 g (63% of theory) of 3-{1-[2-(tetrahydropyran-2-yloxy)-phenyl]-2-methoxyethen-1-yl}-5,6-dihydro-1,4,2-dioxazine are obtained.

Workup

temperaturethe mixture is refluxed at the boil for 12 hours
concentrationThe mixture is concentrated under reduced pressure
customthe residue is partitioned between water and ethyl acetate
customThe organic phase is separated off
dry with materialdried over sodium sulphate
customThe residue is chromatographed on silica gel

Sources & evidence

ORD record: ord-d9ba04cf91d64f58897ba6b9f1f836cc
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06407233B1

Reaction notes

Loading…