Acetic Acid → 2-Methyl-5-(3,4,5-trimethoxyphenyl)pentan-2-ol

HRID 1250962ノート

反応式

HRID 1250962 の反応式
[Li].Br[CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1.[CH3:18][C:19]([CH3:21])=[O:20].C(O)(=O)C>O1CCCC1>[CH3:18][C:19]([OH:20])([CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[C:8]([O:16][CH3:17])[CH:7]=1)[CH3:21]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 180AcetoneHCID 3028194LithiumHCID 226096115-(3-Bromopropyl)-1,2,3-trimethoxybenzene

生成物 1

HCID 226095282-Methyl-5-(3,4,5-trimethoxyphenyl)pentan-2-ol収率 24.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To anhydrous tetrahydrofuran (10 ml) stirred in an ice bath under nitrogen were added 104 mg (15 mmol) of lithium, 3.9 g (14 mmol) of 1-bromo-3-(3,4,5-trimethoxyphenyl)propane (1), and a solution of 0.95 ml (13 mmol) of acetone in tetrahydrofuran (10 ml). After the mixture was stirred for 17 hours at room temperature, a 2% aqueous solution of acetic acid (50 ml) chilled with ice was added to conduct extraction with diethyl ether. An organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated saline solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil (4.1 g) was purified by column chromatography on silica gel, thereby obtaining 860 mg (yield: 24%) of 2-methyl-5-(3,4,5-trimethoxyphenyl)pentan-2-ol.

後処理

  1. additionwas added
  2. extractionextraction with diethyl ether
  3. washAn organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  4. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant crude oil (4.1 g) was purified by column chromatography on silica gel

出典と根拠

ORDレコード
ord-c97ce0cd51f946e19ad2ffb01d22343c
出典データセット
uspto-grants-2002_01
特許番号
US06340682B1

反応ノート

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