(4-Fluorobenzyl)triphenylphosphonium chloride → 4-(4-(4-Fluorobenzylidene)-1-piperidinyl)benzonitrile

HRID 731543

反応式

HRID 731543 の反応式
[Cl-].[F:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.[Li]CCCC.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][C:45](=O)[CH2:44][CH2:43]2)=[CH:38][CH:37]=1)#[N:35]>C1COCC1>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH:7]=[C:45]2[CH2:46][CH2:47][N:42]([C:39]3[CH:40]=[CH:41][C:36]([C:34]#[N:35])=[CH:37][CH:38]=3)[CH2:43][CH2:44]2)=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 2733554(4-Fluorobenzyl)triphenylphosphonium chlorideHCID 110198874-(4-Oxopiperidin-1-yl)benzonitrileHCID 178418339Butyllithium

生成物 1

HCID 591866134-(4-(4-Fluorobenzylidene)-1-piperidinyl)benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of the 4-fluorobenzyl triphenylphosphonium chloride (0.737 g, 1.81 mmol) in THF (10 mL) was treated with nBuLi (724 μL of a 1.6M solution in hexanes, 1.81 mmol) at 0° C., treated with 1-(4′-cyanophenyl)-4-oxopiperidine (prepared according to the procedure described in Synthesis 1981, 606-608, 0.300 g, 1.51 mmol), and gradually warmed to room temperature overnight. The reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl and the aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The resulting residue was purified by silica gel chromatography eluting with 10% ethyl acetate in hexanes to give the desired product. (0.268 g, 61%). MS (ESI) m/e 292 (M+H)+.

後処理

  1. customprepared
  2. customdescribed in Synthesis 1981, 606-608, 0.300 g, 1.51 mmol), and
  3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous NH4Cl
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel chromatography
  9. washeluting with 10% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-7b558142890d4dbbb5ea4e86413657e8
出典データセット
uspto-grants-2009_09
特許番号
US07585858B2

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