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

HRID 356929

반응식

HRID 356929 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-7f76afb33c724a78ab924db6c1a151ba
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05840724

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