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

HRID 327598노트

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HRID 327598 반응식
[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

참가 물질

5

반응물 4

HCID 8028Tetrahydrofuran2회HCID 24758Sodium hydrideHCID 15052470Benzaldehyde, 3-(cyclopentyloxy)-4-nitro-HCID 53413272Trimethylphosphonoacetate

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ac7b32b260d42f9938d6543fa75edb5
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05274002

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