Hydrochloric Acid → (2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methanol

HRID 1877035

반응식

HRID 1877035 반응식
[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]=[O:8].Br[Mg][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(OCC)C.Cl.O>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][C:6]=1[CH:7]([CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[OH:8]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27953132-Methyl-5-phenyl-3-furaldehydeHCID 178467675HCID 178467675, 화합물

생성물 1

HCID 68514112(2-methyl-5-phenylfuran-3-yl)(tetrahydro-2H-pyran-4-yl)methanol수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-methyl-5-phenylfuran-3-carbaldehyde (1.9 g) in tetrahydrofuran (30 mL) was added dropwise bromo(tetrahydro-2H-pyran-4-yl)magnesium-diethyl ether solution (30 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 30 min. The reaction mixture was treated with 1N hydrochloric acid, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (10% ethyl acetate/hexane to 40% ethyl acetate/hexane) to give the title compound (2.3 g, 86%) as an oil.

후처리

  1. additionafter the completion of the dropwise addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column (10% ethyl acetate/hexane to 40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-9ee7c736d71249d8b6d97a2b035b8719
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309580B2

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