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

HRID 1051

반응식

HRID 1051 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-87b01b59f727440086967c46a538d8dc
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723479

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