(E)-N-(3-phenyl-2-buten-1-yl)benzamide → (5RS, 6SR)-2,6-diphenyl-6-methyl-5,6-dihydro-4H-1,3-oxazin-5-ol

HRID 982263Notes

Reaction equation

HRID 982263 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:11]([OH:14])[CH2:12][N:13]=1.[C:21]1(/C(/C)=C/CNC(=O)C2C=CC=CC=2)C=CC=CC=1>>[CH3:21][C:10]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:9][C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)=[N:13][CH2:12][CH:11]1[OH:14]

Participants

3

Reactant 2

HCID 14650565(E)-N-(3-phenyl-2-buten-1-yl)benzamideHCID 14650610(5RS, 6SR)-2-(2-fluorophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol

Product 1

HCID 14650626(5RS, 6SR)-2,6-diphenyl-6-methyl-5,6-dihydro-4H-1,3-oxazin-5-ol

Procedure

(5RS, 6SR)-6-Methyl-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazin-5-ol may be obtained in the following manner: working as in Example 22 for the preparation of (5RS, 6SR)-2-(2-fluorophenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-ol, but starting with (E)-N-(3-phenyl-2-buten-1-yl)benzamide (4.2 g), a 0.35 M solution (48 cc) of 3-chloroperbenzoic acid in dichloromethane and boron trifluoride etherate (2.6 g), and after purification of the oil obtained by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica (0.2-0.063 mm), eluting with a mixture of cyclohexane and ethyl acetate (60:40 by volume) and collecting 30-cc fractions, fractions 9 to 17 being combined and concentrated to dryness under reduced pressure (4 kPa) at 45° C., followed by recrystallization of the residue obtained in isopropyl ether, (5RS, 6SR)-6-methyl-2,6-diphenyl-5,6-dihydro-4H-1,3-oxazin-5-ol (1.65 g, m.p. 130° C.) is obtained.

Workup

  1. customa 0.35 M solution (48 cc) of 3-chloroperbenzoic acid in dichloromethane and boron trifluoride etherate (2.6 g), and after purification of the oil
  2. customobtained by chromatography on a column (height: 35 cm; diameter: 3 cm) of silica (0.2-0.063 mm)
  3. washeluting with a mixture of cyclohexane and ethyl acetate (60:40 by volume)
  4. customcollecting 30-cc fractions, fractions 9 to 17 being
  5. concentrationconcentrated to dryness under reduced pressure (4 kPa) at 45° C.
  6. customfollowed by recrystallization of the residue
  7. customobtained in isopropyl ether

Sources & evidence

ORD record
ord-a2c3f6e0a1a04f759ce9fa0685218fa7
Source dataset
uspto-grants-1991_02
Patent number
US04994569

Reaction notes

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