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Homoallyl bromide → 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhept-6-en-3-ol

HRID 1274877
Notes
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Reaction equation

HRID 1274877 reaction equation
Br[CH2:2][CH2:3][CH:4]=[CH2:5].[Mg].[CH3:7][C:8]1[O:13][CH2:12][N:11]([C:14]([CH3:18])([CH3:17])[CH:15]=[O:16])[C:10](=[O:19])[C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:7][C:8]1[O:13][CH2:12][N:11]([C:14]([CH3:17])([CH:15]([OH:16])[CH2:5][CH2:4][CH:3]=[CH2:2])[CH3:18])[C:10](=[O:19])[C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 21241Homoallyl bromide2×HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 221182842-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionaldehyde

Product 1

HCID 221183422-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhept-6-en-3-olYield 145.5%

Reagents, catalysts & solvents

2
HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

4-Bromobut-1-ene (approximately 0.2 g) was added to a suspension of magnesium (0.17 g) in tetrahydrofuran, under an inert atmosphere at 20° C. Once the reaction had initiated, further 4-bromobut-1-ene (approximately 0.67 g) in tetrahydrofuran was added over 10 minutes. After refluxing for 1 hour, the mixture was cooled to -5° C. and a solution of 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropionaldehyde (1.00 g) in tetrahydrofuran was added over 20 minutes. After stirring for 18 hours, ammonium chloride and ethyl acetate were added and the organic phase washed (brine), dried (magnesium sulphate) and evaporated to give 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylhept-6-en-3-ol (0.68 g) as a white solid, m.p. 74-75° C.

Workup

  1. temperatureAfter refluxing for 1 hour
  2. washthe organic phase washed (brine)
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated

Sources & evidence

ORD record
ord-63379e61848a4bde93aa86cb7eadc988
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06159902

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes