3-Chlorocyclopent-1-ene → 3-Cyclopent-2-enyloxy-4-methoxybenzaldehyde

HRID 356929

反応式

HRID 356929 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[H-].[Na+].Cl[CH:15]1[CH2:19][CH2:18][CH:17]=[CH:16]1>CN(C)C=O>[CH:19]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:18][CH2:17][CH:16]=[CH:15]1

参加物

5

反応物 3

HCID 72973-Chlorocyclopent-1-eneHCID 12127IsovanillinHCID 24758Sodium hydride

生成物 1

HCID 221458283-Cyclopent-2-enyloxy-4-methoxybenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-hydroxy-4-methoxybenzaldehyde (14.20 g) in dry dimethylformamide (300 mL) is treated portionwise with sodium hydride (60% dispersion in oil; 3.70 g) at room temperature under nitrogen. 3-Chlorocyclo-pentene (9.6 mL) is added and the resulting mixture is stirred overnight. The solvent is then removed under reduced pressure and the residue is partitioned between water (500 mL) and dichloromethane (500 mL) and the aqueous layer is further extracted with dichloromethane (500 mL). The combined organic extracts are dried and evaporated under reduced pressure and the residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (1:1 v/v), to give 3-cyclopent-2-enyloxy-4-methoxybenzaldehyde, in the form of a pale brown oil (11.2 g).

後処理

  1. customThe solvent is then removed under reduced pressure
  2. customthe residue is partitioned between water (500 mL) and dichloromethane (500 mL)
  3. extractionthe aqueous layer is further extracted with dichloromethane (500 mL)
  4. customThe combined organic extracts are dried
  5. customevaporated under reduced pressure
  6. washeluting with a mixture of ethyl acetate and pentane (1:1 v/v)

出典と根拠

ORDレコード
ord-7f76afb33c724a78ab924db6c1a151ba
出典データセット
uspto-grants-1998_11
特許番号
US05840724

関連ノート

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