Diethyl dipicolinate → 2-Pyridinecarboxylic acid, 6-(hydroxymethyl)-, ethyl ester

HRID 2356607

反応式

HRID 2356607 の反応式
[BH4-].[Na+].[N:3]1[C:8]([C:9](OCC)=[O:10])=[CH:7][CH:6]=[CH:5][C:4]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(O)C>[OH:10][CH2:9][C:8]1[N:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 254510Diethyl dipicolinateHCID 4311764Sodium borohydride2 回

生成物 1

HCID 109211412-Pyridinecarboxylic acid, 6-(hydroxymethyl)-, ethyl ester収率 80.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

11.4 g (0.3 mol) of sodium borohydride was added in one portion to a stirred solution of 111.5 g (0.5 mol) of diethyl 2,6-pyridinedicarboxylate in 1 litre of ethanol and stirred for 6 hours when a further 2.85 g (0.075 mol) of sodium borohydride were added and the mixture stirred overnight before being evaporated. The residue was dissolved in 800 ml dichloromethane and washed with water. The aqueous was extracted with 4×50 ml of dichloromethane. The combined organics were dried, evaporated and combined with the product from reaction 1 (13.1 g). The combined material was washed through a pad of silica on a large sinter with ethyl acetate (2 litres) which was evaporated and triturated with ether and filtered off to give 72.6 g of a white solid. The MLS (mother liquors) were evaporated and biotaged (chromatographed) [ethyl acetate/hexane (3:1)] to give a further 2.9 g of product.

後処理

  1. additionwere added
  2. custombefore being evaporated
  3. dissolutionThe residue was dissolved in 800 ml dichloromethane
  4. washwashed with water
  5. extractionThe aqueous was extracted with 4×50 ml of dichloromethane
  6. customThe combined organics were dried
  7. customevaporated
  8. customcombined with the product from reaction 1 (13.1 g)
  9. washThe combined material was washed through a pad of silica on a large sinter with ethyl acetate (2 litres) which
  10. customwas evaporated
  11. customtriturated with ether
  12. filtrationfiltered off

出典と根拠

ORDレコード
ord-74c78d92a25d4b519ffe38f4fcb28612
出典データセット
uspto-grants-2010_07
特許番号
US07759369B2

関連ノート

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