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

HRID 1159407ノート

反応式

HRID 1159407 の反応式
[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]

参加物

7

反応物 4

HCID 1183VanillinHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydride

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b1f8b3ccb52b422bb7c8da4fae7d3133
出典データセット
uspto-grants-2010_10
特許番号
US07812040B2

反応ノート

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