Tetrahydrofuran → Methyl 3-(3-cyclopentoxy-4-nitrophenyl)-E-propenoate

HRID 1073743ノート

反応式

HRID 1073743 の反応式
[H-].[Na+].C[C:4](P(OC)(O)=O)([C:6]([O-:8])=[O:7])[CH3:5].[CH:14]1([O:19][C:20]2[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=2[N+:28]([O-:30])=[O:29])C=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.O1CCC[CH2:32]1>>[CH:14]1([O:19][C:20]2[CH:21]=[C:22](/[CH:5]=[CH:4]/[C:6]([O:8][CH3:32])=[O:7])[CH:25]=[CH:26][C:27]=2[N+:28]([O-:30])=[O:29])[CH2:15][CH2:16][CH2:17][CH2:18]1

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 15052470Benzaldehyde, 3-(cyclopentyloxy)-4-nitro-HCID 53413272Trimethylphosphonoacetate

生成物 1

HCID 15052471Methyl 3-(3-cyclopentoxy-4-nitrophenyl)-E-propenoate

実験手順

To a stirred suspension of 0.89 g (22.3 mmol) of a 50% oil suspension of sodium hydride (previously washed with three, 10 mL portions of hexane) in 100 mL of dry tetrahydrofuran under a nitrogen atmosphere was added dropwise at room temperature 2.54 mL (15.7 mmol) of trimethylphosphonoacetate in 100 mL of dry tetrahydrofuran over a 30 minute period. The white suspension was stirred for an additional 10 minutes after which time 3.35 g (14.2 mmol) of 3-cyclopentoxy-4-nitrobenzaldehyde in 50 mL of dry tetrahydrofuran was added dropwise over a 20 minute period. The final reaction mixture was stirred for an additional hour after which time the mixture was quenched with excess saturated ammonium chloride. The mixture was extracted with three, 50 mL portions of methylene chloride and the combined organic fractions were washed with one, 50 mL portion of saturated sodium chloride, dried over magnesium sulfate and concentrated. Liquid chromatography of the crude product over 130 g of silica gel eluting with 50% ethyl acetate in hexane provided the desired, analytically pure solid.

後処理

  1. washpreviously washed with three, 10 mL portions of hexane) in 100 mL of dry tetrahydrofuran under a nitrogen atmosphere
  2. additionwas added dropwise over a 20 minute period
  3. customThe final reaction mixture
  4. customwas quenched with excess saturated ammonium chloride
  5. extractionThe mixture was extracted with three, 50 mL portions of methylene chloride
  6. washthe combined organic fractions were washed with one, 50 mL portion of saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-65a5295c593d4bc7b32696ecea514881
出典データセット
uspto-grants-1990_11
特許番号
US04971959

反応ノート

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