Diethyl Ether → 2-Propyl-4-trifluoromethyl-benzaldehyde

HRID 1042468ノート

反応式

HRID 1042468 の反応式
CON(C)[C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[CH2:15][CH2:16][CH3:17].[H-].[H-].[H-].[H-].[Li+].[Al+3].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+].CCOCC>C1COCC1>[CH2:15]([C:6]1[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:18])[CH2:16][CH3:17]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 58111816N-methoxy-N-methyl-2-propyl-4-trifluoromethyl-benzamide

生成物 1

HCID 866499632-Propyl-4-trifluoromethyl-benzaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

To a solution of N-methoxy-N-methyl-2-propyl-4-trifluoromethyl-benzamide (230 mg, 0.84 mmol) in THF (15 mL) was added dropwise 1.0M LiAlH4 (0.42 mL, 0.42 mmol) at −78° C. The mixture was warmed up to −20° C. and stirred for 30 mins. An aqueous solution of sodium potassium tartrate (10% w/v) was added to the reaction mixture and the resulting mixture was vigorously stirred for 30 mins, to which was added Et2O. After separation of two phases, the aqueous layer was extracted three times with ether and the combined organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The product was vacuum dried to yield the 2-propyl-4-trifluoromethyl-benzaldehyde.

後処理

  1. stirringthe resulting mixture was vigorously stirred for 30 mins, to which
  2. customAfter separation of two phases
  3. extractionthe aqueous layer was extracted three times with ether
  4. washthe combined organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customdried

出典と根拠

ORDレコード
ord-c943b3a436714b6ba4a8e3e087f7c775
出典データセット
uspto-grants-2013_10
特許番号
US08557872B2

反応ノート

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