Hydrochloric Acid → HCID 10197841、化合物

HRID 326602

反応式

HRID 326602 の反応式
C([Li])CCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[N+:12]([C:15]1[CH:16]=C(C=C[CH:22]=1)C=O)([O-:14])=[O:13].Cl>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.O1CCCC1.C(OCC)(=O)C>[CH2:8]([C:9]1[CH:22]=[C:15]([N+:12]([O-:14])=[O:13])[CH:16]=[CH:11][CH:10]=1)[CH:7]=[CH2:6]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 74493-NitrobenzaldehydeHCID 8058HexaneHCID 178418339Butyllithium

生成物 1

HCID 10197841HCID 10197841、化合物収率 70.6%

試薬・触媒・溶媒 3

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)触媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a suspension of ethyltriphenylphosphonium bromide (22 g) in tetrahydrofuran (150 ml) at -78° C. was added dropwise a solution of n-butyllithium in hexane (59.3 mmol). The mixture was left to warm to room temperature over 30 minutes, then cooled to -78° C. and a solution of 3-nitrobenzaldehyde (7.5 g) in tetrahydrofuran (50 ml) was added dropwise. The reaction was left to warm to room temperature over 1 hour, poured into 2M hydrochloric acid (100 ml) and ethyl acetate (100 ml). The separated aqueous layer was extracted with ethyl acetate, the organic layers were combined and washed with water, saturated sodium bicarbonate (2×50 ml), brine (2×50 ml) and dried over magnesium sulphate. The solvent was removed under reduced pressure and the crude product purified by column chromatography to give 3-(2-propenyl)nitrobenzene (5.72 g). δ(60 MHz, CDCl3) 1.9 (3H,2d, CH3), 5.9 (1 H, m, =CH--CH3), 6.3 (1H, 2d, AR--CH) and 7.3-8.1 (4H, m, ArH). To a solution of the above 3-(2-propenyl)-nitrobenzene (5.7 g) in ethyl acetate (20 ml) was added 10% palladium on carbon (0.57 g). This mixture was hydrogenated at 50 psi for 2 hours at room temperature, filtered through Hyflo and solvent evaporated to yield the crude product which was purified by column chromatography to give 3-propylaniline (4.7 g), δ (60 MHz, CDCl3) 0.9 (3H, t, CH3), 1.5 (2H, m, CH2CH3), 2.4 (2H, t, CH2CH2CH3), 3.4 (2H, bs, NH2) and 6.1 to 7.0 (4H, m, ArH).

後処理

  1. waitThe mixture was left
  2. temperaturecooled to -78° C.
  3. waitThe reaction was left
  4. temperatureto warm to room temperature over 1 hour
  5. extractionThe separated aqueous layer was extracted with ethyl acetate
  6. washwashed with water, saturated sodium bicarbonate (2×50 ml), brine (2×50 ml)
  7. dry with materialdried over magnesium sulphate
  8. customThe solvent was removed under reduced pressure
  9. customthe crude product purified by column chromatography

出典と根拠

ORDレコード
ord-ad0b0bf431894523a613bccfdc04948d
出典データセット
uspto-grants-1993_12
特許番号
US05270309

関連ノート

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