Triphenylphosphine → HCID 10244920, compound

HRID 2084814Notes

Reaction equation

HRID 2084814 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Br:13][C:14]1[C:21]([OH:22])=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][C:15]=1[CH:16]=[O:17].[CH:25]1(O)[CH2:30][CH2:29][CH2:28][CH:27]=[CH:26]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O.C1COCC1>[Br:13][C:14]1[C:21]([O:22][CH:30]2[CH2:29][CH2:28][CH2:27][CH:26]=[CH:25]2)=[C:20]([O:23][CH3:24])[CH:19]=[CH:18][C:15]=1[CH:16]=[O:17]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 131982-Cyclohexen-1-OLHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2240112-Bromoisovanillin

Product 1

HCID 10244920HCID 10244920, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (2.7 ml) was dropwise added to a mixture of 2-bromo-3-hydroxy-4-methoxy-benzaldehyde (4.0 g), THF (80 ml), 2-cyclohexen-1-ol (1.2 ml), and triphenylphosphine (4.5 g) under ice-cooling, followed by stirring at room temperature for 2 hours. The mixture was poured into water followed by extraction with ether. The organic layer was washed with a 1N aqueous solution of sodium hydroxide and with a saturated saline, and dried over sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (hexane:ethyl acetate=10:1 and 5:1) to give Compound IIn-a (1.8 g, 47%) as a pale-yellow oily substance.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ether
  3. washThe organic layer was washed with a 1N aqueous solution of sodium hydroxide and with a saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (hexane:ethyl acetate=10:1 and 5:1)
  7. customto give Compound IIn-a (1.8 g, 47%) as a pale-yellow oily substance

Sources & evidence

ORD record
ord-04e4ccf65b8b451a8e3c97456df4d63a
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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