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Triacetoxyperiodinane → 1-(4-(4-Methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde

HRID 417997
ノート
印刷プレビュー

反応式

HRID 417997 の反応式
[OH:1][CH2:2][C:3]1([C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC.[OH-].[Na+]>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:12][CH2:11][N:10]([C:8]([C:3]3([CH:2]=[O:1])[CH2:4][CH2:5][CH2:6][CH2:7]3)=[O:9])[CH2:15][CH2:14]2)=[CH:21][CH:20]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 66651026(1-Hydroxymethyl-cyclopentyl)-(4-(4-methylphenyl)piperazin-1-yl)-methanone

生成物 1

HCID 866357821-(4-(4-Methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde収率 105%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒
HCID 14798
Sodium Hydroxide
溶媒

実験手順

(1-Hydroxymethyl-cyclopentyl)-(4-(4-methylphenyl)piperazin-1-yl)-methanone from the previous step (1.57 g, 5.22 mmol) was dissolved in DCM (40 mL). Dess-Martin periodinane (3.06 g, 7.22 mmol) was added and the reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture diluted with Et2O (100 mL) and 1M aq NaOH solution (50 mL) was added. The reaction mixture was stirred for 20 minutes and then the organic layer was separated and washed with 1M aq NaOH solution (50 mL), water (50 mL), dried (MgSO4) and concentrated in vacuo to give 1-(4-(4-methylphenyl)-piperazine-1-carbonyl)-cyclopentanecarbaldehyde (1.64 g, 105%) as a brown oil which was used without further purification.

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 20 minutes
  3. customthe organic layer was separated
  4. washwashed with 1M aq NaOH solution (50 mL), water (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d0b34e02926f407f95cd2010c108d29b
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093248B2

反応ノート

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