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

HRID 551687

反応式

HRID 551687 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-915e8305ead74a959ddda63652cb621c
出典データセット
uspto-grants-2011_05
特許番号
US07947738B2

関連ノート

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