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

HRID 1250962노트

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HRID 1250962 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c97ce0cd51f946e19ad2ffb01d22343c
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06340682B1

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