Hydrochloric Acid → 2-(Naphthalen-1-yl)propane-1,3-diol

HRID 1613333

反応式

HRID 1613333 の反応式
[C:1]1([CH:11]([C:17](OCC)=[O:18])[C:12](OCC)=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].Cl.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O1CCOCC1.O>[C:1]1([CH:11]([CH2:12][OH:13])[CH2:17][OH:18])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14812Phosphorus oxide (P4O10)HCID 240505Diethyl 2-(1-naphthyl)malonateHCID 4311764Sodium borohydride

生成物 1

HCID 146425962-(Naphthalen-1-yl)propane-1,3-diol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

50 g (175 mmol) of diethyl 2-(naphthalen-1-yl)propanedioate in 310 ml of dioxane and 300 ml of water are stirred at ambient temperature; an excess (2.2 mol, or 84 g) of sodium borohydride is then added in portions; the mixture is stirred for 8 h, and the products are left in contact for 2 days. The mixture is then hydrolysed, with stirring, while introducing crushed ice and 3N hydrochloric acid until an acidic pH is obtained. The mixture is extracted with diethyl ether, the organic phase is evaporated, and the residual oil is purified by chromatography on a silica gel column eluted with ethyl acetate. After evaporation and drying at 40° C. in the presence of phosphorus pentoxide, 18.5 g (91 mmol) of product are isolated. Melting point: 58-60° C.

後処理

  1. waitthe products are left in contact for 2 days
  2. stirringhydrolysed, with stirring
  3. additionwhile introducing
  4. customis obtained
  5. extractionThe mixture is extracted with diethyl ether
  6. customthe organic phase is evaporated
  7. customthe residual oil is purified by chromatography on a silica gel column
  8. washeluted with ethyl acetate
  9. customAfter evaporation
  10. customare isolated

出典と根拠

ORDレコード
ord-a6dd361719084b199d66c76a2f539123
出典データセット
uspto-grants-1993_03
特許番号
US05192797

関連ノート

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