Water → 6-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarbaldehyde

HRID 2377199ノート

反応式

HRID 2377199 の反応式
[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22](OC)=[O:23])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C.ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)=[CH:13][C:12]([CH:22]=[O:23])=[CH:11][C:10]=1[C:26]([CH3:29])([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 12084817Methyl 6-benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarboxylateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 120848186-Benzyloxy-5-tert-butyl-4'-methyl-3-biphenylcarbaldehyde収率 85%

試薬・触媒・溶媒 3

HCID 178418406HCID 178418406、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

1 g (2.6 mmol) of methyl 6-benzyloxy-5-tert-butyl-4′-methyl-3-biphenylcarboxylate is dissolved in 40 mL of anhydrous ethyl ether, and the medium is cooled to 0° C. 130 mg (3.3 mmol) of lithium aluminum hydride are added and the reaction medium is stirred for 1 hour. The reaction is hydrolysed by sequential addition of 130 μL of water, 130 μL of 15% sodium hydroxide solution and 400 μL of water. The reaction medium is filtered and the filtrate is concentrated under reduced pressure. The residue obtained is dissolved in 30 mL of dichloromethane, and 2 g (23 mmol) of manganese dioxide are added. The medium is refluxed for 5 hours, and filtered through Celite. A yellow oil is obtained (m=780 mg; yield=85%).

後処理

  1. filtrationThe reaction medium is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe residue obtained
  4. temperatureThe medium is refluxed for 5 hours
  5. filtrationfiltered through Celite
  6. customA yellow oil is obtained (m=780 mg; yield=85%)

出典と根拠

ORDレコード
ord-ade757147fc0433d88be1d0a13bf61c9
出典データセット
uspto-grants-2008_12
特許番号
US07468457B2

反応ノート

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