Vanillin → 2-Methoxy-4-(pyrrolidin-1-ylmethyl)phenol

HRID 1159407노트

반응식

HRID 1159407 반응식
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.O=[CH:21][C:22]1[CH:30]=[CH:29][C:27]([OH:28])=[C:24]([O:25][CH3:26])[CH:23]=1.[OH-].[Na+]>C(Cl)Cl.O>[CH3:26][O:25][C:24]1[CH:23]=[C:22]([CH2:21][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:30]=[CH:29][C:27]=1[OH:28]

참가 물질

7

반응물 4

HCID 1183VanillinHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 686193052-Methoxy-4-(pyrrolidin-1-ylmethyl)phenol수율 75%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

NaB(OAc)3H (8.7 g, 0.041 mol) was added in portions for 30 min to a mixture of pyrrolidine (3.4 mL, 0.041 mol) and vanillin (5 g, 0.033 mol) in CH2Cl2 (50 mL) under vigorous stirring and cooling with an ice bath in an atmosphere of argon. The mixture was stirred for 2 h and cooled. Then 10 N NaOH (4.1 mL) and water (30 mL) were added. The organic layer was separated; the aqueous one was extracted with chloroform (2×50 mL). The organic fractions were evaporated. The residue was distributed between water and CH2Cl2. Concentrated HCl (2.98 mL) was added. The organic layer was separated and discarded. The aqueous one was alkalized with 10 N NaOH to pH 6 and extracted with chloroform (2×100 mL). The combined extracts were dried with Na2SO4, and evaporated to give the title compound (5.1 g, 75%) was obtained as white crystals. 1H-NMR (400 MHz)-data (dmso-d6): 8.72 (s, 1H ArOH), 6.81-6.84 (m, 1H, Ar—H), 6.64-6.70 (m, 2H, Ar—H), 3.74 (s, 3H, ArOCH3), 3.43 (s, 2H, ArCH2), 2.36-2.41 (m, 4H, pyrrolidine (CH2)2N), 1.64-1.70 (m, 4H, CH2CH2CH2CH2).

후처리

  1. temperaturecooling with an ice bath in an atmosphere of argon
  2. stirringThe mixture was stirred for 2 h
  3. temperaturecooled
  4. customThe organic layer was separated
  5. extractionthe aqueous one was extracted with chloroform (2×50 mL)
  6. customThe organic fractions were evaporated
  7. additionConcentrated HCl (2.98 mL) was added
  8. customThe organic layer was separated
  9. extractionextracted with chloroform (2×100 mL)
  10. dry with materialThe combined extracts were dried with Na2SO4
  11. customevaporated

출처 및 근거

ORD 기록
ord-b1f8b3ccb52b422bb7c8da4fae7d3133
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812040B2

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