Triethylamine → 4-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

HRID 1869347ノート

反応式

HRID 1869347 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH2:11][OH:12])[CH:7]=1.C(N(CC)CC)C.[Cl-].[NH4+].C(OC)(C)(C)C>ClCCl.CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH3:21])=[C:6]([C:8]([CH3:19])([CH3:18])[CH2:9][C:10]([OH:17])([C:13]([F:16])([F:15])[F:14])[CH:11]=[O:12])[CH:7]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 25517Ammonium ChlorideHCID 179891794-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol

生成物 1

HCID 179891754-(5-Bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal収率 79.9%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 6344Dichloromethane溶媒

実験手順

1.13 g (3.06 mmol) of 4-(5-bromo-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol is added in 20 ml of dichloromethane and 5.4 ml of DMSO. After mixing with 1.55 g (15.32 mmol) of triethylamine and 975.28 mg (6.13 mmol) of SO3/pyridine complex, the batch is stirred overnight at room temperature. After TLC, another spatula tip full of SO3/pyridine complex is added, and it is further stirred for several hours. The reaction mixture is mixed with saturated ammonium chloride solution and shaken out three times with methyl tert-butyl ether. The combined organic extracts are washed with water and brine. After the solvent is dried and spun off, the residue is chromatographed on a Flashmaster. 902.7 mg (79.81%) of the desired aldehyde (together with the Desbrom compound) is isolated.

後処理

  1. additionAfter TLC, another spatula tip full of SO3/pyridine complex is added
  2. stirringit is further stirred for several hours
  3. washThe combined organic extracts are washed with water and brine
  4. customAfter the solvent is dried
  5. customthe residue is chromatographed on a Flashmaster

出典と根拠

ORDレコード
ord-60961f820fbb49ffbf4a082b3ff1957d
出典データセット
uspto-grants-2009_12
特許番号
US07638515B2

反応ノート

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