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

HRID 655900ノート

反応式

HRID 655900 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
45 °C

実験手順

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 stirred 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.

後処理

  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)

出典と根拠

ORDレコード
ord-d9f3f19afdd14e95a2ded9984cc47c2b
出典データセット
uspto-grants-2011_12
特許番号
US08071626B2

反応ノート

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