Triphenylphosphine → 4-{3-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalene-1-carbaldehyde

HRID 479144

반응식

HRID 479144 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH3:18])=[C:12]([CH2:14][CH2:15][CH2:16][OH:17])[N:13]=2)=[CH:5][CH:4]=1.O[C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH:30]=[O:31])=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:10][C:11]([CH3:18])=[C:12]([CH2:14][CH2:15][CH2:16][O:17][C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]([CH:30]=[O:31])=[CH:22][CH:21]=3)[N:13]=2)=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 3442904-Hydroxy-1-naphthaldehydeHCID 5363146Diisopropyl azodicarboxylateHCID 180035253-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propan-1-ol

생성물 1

HCID 180035974-{3-[2-(4-Methoxy-phenyl)-5-methyl-oxazol-4-yl]-propoxy}-naphthalene-1-carbaldehyde

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

g of the above prepared 3-[2-(4-methoxy-phenyl)-5-methyl-oxazol-4-yl]-propan-1ol (4.04 mmol) was dissolved in 21 ml of toluene and treated successively at 0° C. with 0.696 g of 4-hydroxy-naphthalene-1-carbaldehyde (4.04 mmol), 1.061 g of triphenylphosphine (4.04 mmol), and 0.818 g (4.04 mmol) of DIAD. The cooling bath was then removed and stirring continued for 3 h. Pouring onto crashed ice, twofold extraction with AcOEt, washing with 3N NaOH and water, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, hexane/AcOEt=7/3) left finally 1.084 g of the title compound as light yellow gum.

후처리

  1. customThe cooling bath was then removed
  2. additionPouring
  3. extractionice, twofold extraction with AcOEt
  4. washwashing with 3N NaOH and water
  5. dry with materialdrying over magnesium sulfate, and evaporation of the solvents
  6. waitleft finally 1.084 g of the title compound as light yellow gum

출처 및 근거

ORD 기록
ord-744c70bc541d45089c2e43a675e97ae7
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642389B2

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