Potassium Carbonate → Isovanillin

HRID 332581

반응식

HRID 332581 반응식
NC1C=CC(CC2C=CC(OC)=C(C=2)OC2C=C(C=CC=2)C#N)=CC=1.COC(=O)[O:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39]C2C=CC=C(C#N)C=2)[CH:32]=1.CC1(C)C(C)(C)OB(C2C=CC(N)=CC=2)O1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)CCCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+].CN(C)C=O>[OH:39][C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][C:34]=1[O:37][CH3:38])[CH:30]=[O:29]

참가 물질

8

반응물 5

HCID 11430Potassium CarbonateHCID 27334141,5-Bis(diphenylphosphino)pentaneHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 577011053-[5-(4-Amino-benzyl)-2-methoxy-phenoxy]-benzonitrileHCID 57701117Carbonic acid 3-(3-cyano-phenoxy)-4-methoxy-benzyl ester methyl ester

생성물 1

HCID 12127Isovanillin

시약·촉매·용매 2

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-촉매HCID 6228Dimethylformamide용매

반응 조건

온도
85 °C

실험 절차

3-[5-(4-Amino-benzyl)-2-methoxy-phenoxy]-benzonitrile P-15. In an 8 mL vial equipped with a stir bar was placed (18) (250 mg, 0.798 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (192 mg, 0.878 mmol), potassium carbonate (331 mg, 2.39 mmol), 1,5-bis(diphenylphosphino)pentane (105 mg, 0.239 mmol), and dimethylformamide (4.5 mL). The mixture was degassed with nitrogen for 15 minutes and allylpalladium(II) chloride dimer (43.8 mg, 0.120 mmol) was added. The mixture was heated to 85° C. for 18 hours. The reaction mixture was filtered through celite and to the filtrate were added water (30 mL) and saturated ammonium chloride solution (30 mL). After extractions with ethyl acetate (2×75 mL), the organic portions were combined, washed with brine (50 mL), dried (MgSO4) and concentrated. The crude material was purified by silica gel column chromatography utilizing 50% ethyl acetate/hexanes to produce 118 mg (45% yield) of P-15 as a yellow viscous oil. MS (APCI+): 331.1 (M+1), LC-MS: >99%

후처리

  1. customIn an 8 mL vial equipped with a stir bar
  2. customThe mixture was degassed with nitrogen for 15 minutes
  3. filtrationThe reaction mixture was filtered through celite and to the filtrate
  4. additionwere added water (30 mL) and saturated ammonium chloride solution (30 mL)
  5. extractionAfter extractions with ethyl acetate (2×75 mL)
  6. washwashed with brine (50 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9216d16aa2c14bb38a1ce62562d51fc7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877816B2

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