Water → 2,3-Diisopropoxy-4-methoxybenzaldehyde

HRID 9308

反応式

HRID 9308 の反応式
[OH:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]([O-])([O-])=O.[K+].[K+].Br[CH:20]([CH3:22])[CH3:21].O.CCO[C:27]([CH3:29])=O>CN(C=O)C>[CH:20]([O:1][C:2]1[C:9]([O:10][CH:27]([CH3:29])[CH3:13])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])([CH3:22])[CH3:21]

参加物

7

反応物 5

HCID 962WaterHCID 63582-BromopropaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 115573522,3-Dihydroxy-4-methoxybenzaldehyde

生成物 1

HCID 219865542,3-Diisopropoxy-4-methoxybenzaldehyde収率 82%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 21 (26.70 g, 158.7 mmol) in DMF (150 mL) under nitrogen, was added K2CO3 (65.84 g, 476.3 mmol) followed by 2-bromopropane (44.72 mL, 476.3 mmol) and heated to reflux (90° C.) for 12 hours. Water (200 mL) and EtOAc (200 mL) were added to the reaction mixture, the phases were separated, and the aqueous phase was extracted with EtOAc (3×200 mL). The combined organic solutions were dried over MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, elution with hexane) provided 32.85 g (1.30.2 mmol, 82%) of the diusopropyl-protected aldehyde 22 as a yellow oil.

後処理

  1. temperatureheated
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (3×200 mL)
  4. dry with materialThe combined organic solutions were dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification
  7. washby flash column chromatography (silica gel, elution with hexane)

出典と根拠

ORDレコード
ord-fcacfd8cbe564e93b9260f019b289944
出典データセット
uspto-grants-2006_08
特許番号
US07091240B2

関連ノート

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