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Hydrochloric Acid → 2-(2-Cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran

HRID 1051
Notes
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Reaction equation

HRID 1051 reaction equation
[H-].[Na+].[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][O:16][C:17]1[CH:27]=[CH:26][C:20]2[CH:21]=[C:22]([CH:24]=O)[O:23][C:19]=2[CH:18]=1.[C:28]([CH2:30]P(=O)(OCC)OCC)#[N:29].Cl>CN(C)C=O>[C:28]([CH2:30][CH2:24][C:22]1[O:23][C:19]2[CH:18]=[C:17]([O:16][CH2:15][C:5]3[N:6]=[C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[O:8][C:4]=3[CH3:3])[CH:27]=[CH:26][C:20]=2[CH:21]=1)#[N:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 196943726-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-2-benzofurancarbaldehyde

Product 1

HCID 101553132-(2-Cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuranYield 83.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 0.20 g) was gradually added to a solution of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran-2-carbaldehyde (1.50 g) and diethyl cyanomethylphosphonate (0.88 g) in N,N-dimethylformamide (30 ml) at 0° C., followed by stirring at room temperature for 1 hour. The reaction mixture was poured over ice water and neutralized with 2N hydrochloric acid, followed by extraction with ethyl acetate (200 ml). After the ethyl acetate layer was washed with water and dried (MgSO4), palladium-carbon (5%, 0.70 g) was added, followed by catalytic reduction at room temperature under an atmospheric pressure of 1 atm. After the catalyst was filtered off, the filtrate was concentrated; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (2:98, v/v), crystals of 2-(2-cyanoethyl)-6-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzofuran (1.34 g, 83%) were obtained, which was then recrystallized from dichloromethane-hexane to yield colorless prisms having a melting point of 92° to 93° C.

Workup

  1. extractionfollowed by extraction with ethyl acetate (200 ml)
  2. washAfter the ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4), palladium-carbon (5%, 0.70 g)
  4. additionwas added
  5. customfollowed by catalytic reduction at room temperature under an atmospheric pressure of 1 atm
  6. filtrationAfter the catalyst was filtered off
  7. concentrationthe filtrate was concentrated
  8. washFrom the fraction eluted with ethyl acetate-chloroform (2:98

Sources & evidence

ORD record
ord-87b01b59f727440086967c46a538d8dc
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05723479

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes