Water → 1-(cyclohex-2-enyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-ol

HRID 1274883Notes

Reaction equation

Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.[CH3:8][C:9]1[O:14][CH2:13][N:12]([C:15]([CH3:19])([CH3:18])[CH:16]=[O:17])[C:11](=[O:20])[C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OCC)(=O)C.O>O1CCCC1.[Zn]>[CH:2]1([CH:16]([OH:17])[C:15]([N:12]2[C:11](=[O:20])[C:10]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[C:9]([CH3:8])[O:14][CH2:13]2)([CH3:19])[CH3:18])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 1-bromocyclohex-2-ene (7.2 g) in tetrahydrofuran was added dropwise during 0.5 hour to a stirred mixture of 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionaldehyde (4.0 g) and zinc powder (3.2 g) in tetrahydrofuran below -20° C. under an inert atmosphere. The mixture was stirred for 1 hour below -20° C. and warmed to 20° C. Ethyl acetate and water were added and the organic phase washed (brine), dried (magnesium sulphate), evaporated and purified by silica gel column chromatography, eluting with n-hexane/ethyl acetate (5:2) to give 1-(cyclohex-2-enyl)-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropan-1-ol (5.1 g), NMR: 1.41(s,3H), 1.53(s,3H), 1.85(s,3H), 1.40-2.05(6H), 2.24(1H), 3.49(1H), 4.32(d,1H), 5.1 1(d 5.24(d,1H), 5.60(1H), 5.76(1H), 7.20-7.40(5H).

Workup

washthe organic phase washed (brine)
dry with materialdried (magnesium sulphate)
customevaporated
custompurified by silica gel column chromatography
washeluting with n-hexane/ethyl acetate (5:2)

Sources & evidence

ORD record: ord-9275f6f3f37645d983760a3d40042e9f
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06159902

Reaction notes

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