Glycerol → Methyl 3,4-dimethyl-3-hydroxy-6-heptenoate

HRID 551687

반응식

HRID 551687 반응식
[CH3:1][CH:2]([CH2:6][CH:7]=[CH2:8])[C:3](=[O:5])[CH3:4].Br[CH2:10][C:11]([O:13][CH3:14])=[O:12].OCC(CO)O.[Cl-].N>O1CCCC1>[CH3:4][C:3]([OH:5])([CH:2]([CH3:1])[CH2:6][CH:7]=[CH2:8])[CH2:10][C:11]([O:13][CH3:14])=[O:12]

참가 물질

6

반응물 4

HCID 753GlycerolHCID 60984Methyl bromoacetateHCID 124223183-Methylhex-5-en-2-oneHCID 20976574Ammonia chloride

생성물 1

HCID 86646146Methyl 3,4-dimethyl-3-hydroxy-6-heptenoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

3-Methyl-5-hexen-2-one (J. Chem. Soc., Chem. Comm. 19, 1991, 1399) (17 g, 106 mmol) and methyl bromoacetate (24.4 g, 159 mmol) were dissolved in tetrahydrofuran (100 mL), and the solution was added dropwise to a tetrahydrofuran (50 mL) (zinc (10.4 g, 159 mmol) and trimethyl borate (30 mL)) solution under reflux. After reflux for 3 hours, the mixture was cooled to room temperature, and glycerin (30 mL) and a saturated aqueous solution of ammonia chloride (100 mL) were added thereto, followed by two extractions with ethyl acetate. The ethyl acetate layer was washed with saturated saline, then dried, and then concentrated. The residue was purified by silica gel column chromatography (200 g) to obtain the compound of interest as an oil substance (11.7 g, 60%).

후처리

  1. temperatureunder reflux
  2. temperatureAfter reflux for 3 hours
  3. extractionfollowed by two extractions with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated saline
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (200 g)
  8. customto obtain the compound of interest as an oil substance (11.7 g, 60%)

출처 및 근거

ORD 기록
ord-915e8305ead74a959ddda63652cb621c
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947738B2

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