Hydrochloric Acid → 4-(2,4,6-trimethoxyphenyl)-6-(hydroxymethyl)pyridine-2-carboxylic Acid Ethyl Ester

HRID 1097176노트

반응식

HRID 1097176 반응식
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[C:13]1[CH:18]=[C:17]([C:19](OCC)=[O:20])[N:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=1.[BH4-].[Na+].Cl>C(O)C>[CH2:27]([O:26][C:24]([C:15]1[CH:14]=[C:13]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[CH:6][C:5]=2[O:11][CH3:12])[CH:18]=[C:17]([CH2:19][OH:20])[N:16]=1)=[O:25])[CH3:28]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 66814130Diethyl 4-(2,4,6-trimethoxyphenyl)pyridine-2,6-dicarboxylate

생성물 1

HCID 668142714-(2,4,6-trimethoxyphenyl)-6-(hydroxymethyl)pyridine-2-carboxylic Acid Ethyl Ester

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
45 °C

실험 절차

Compound 12 (2.83 g, 7.27 mmol) was suspended in ethanol (140 mL), and the mixture was heated to 45° C. Sodium borohydride (0.29 g) was added, and the mixture was strirred for 1 h and allowed to cool to room temperature. pH of the solution was adjusted to 3 with 6 M HCl and concentrated. The residue was suspended in dichloromethane and washed with sat. NaHCO3. The organic layer was dried over Na2SO4 and purified on silica gel (eluent petroleum ether bp 40-60° C.:ethyl acetate:triethylamine, 2:5:1; v/v/v). ESI-MS: [M+H]+ 348.14 calc. for C18H22NO6+ 348.14.

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. washwashed with sat. NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. custompurified on silica gel (eluent petroleum ether bp 40-60° C.:ethyl acetate:triethylamine, 2:5:1; v/v/v)

출처 및 근거

ORD 기록
ord-23bb373c07134b1ea0fa33120de05272
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143057B2

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