Methanol → N-heptyl-N-ethyl(6-hydroxy)hexanamide

HRID 36147ノート

反応式

HRID 36147 の反応式
[CH2:1]([N:8]([CH2:19][CH3:20])[C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][C:14](OC)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[BH4-].[Na+].CO>C(O)(C)(C)C>[CH2:1]([N:8]([CH2:19][CH3:20])[C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

参加物

5

反応物 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86748668N-heptyl-N-ethyladipamic acid, methyl ester

生成物 1

HCID 22407916N-heptyl-N-ethyl(6-hydroxy)hexanamide収率 35.8%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

A mixture of a solution of 3.1 gms of the N-heptyl-N-ethyladipamic acid, methyl ester in 40 ml of tert-butanol and 800 mg of sodium borohydride is heated to reflux, following which 7.8 ml of methanol is added dropwise. The reaction mixture is stirred at reflux for 18 hours and then partitioned between water and CH2Cl2. After separation, the organic layer is dried over MgSO4, filtered, and concentrated under vacuum. The residue obtained is flash chromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate to yield 1.0 gms of N-heptyl-N-ethyl(6-hydroxy)hexanamide.

後処理

  1. temperatureis heated
  2. temperatureto reflux
  3. additionis added dropwise
  4. temperatureat reflux for 18 hours
  5. custompartitioned between water and CH2Cl2
  6. customAfter separation
  7. dry with materialthe organic layer is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue obtained
  11. customchromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-6a455df6206d4f0fa050d33537601b1c
出典データセット
uspto-grants-1995_05
特許番号
US05412137

反応ノート

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