Hydrochloric Acid → 1,4-Dioxaspiro[4.5]dec-8-yl(2-methyl-5-phenylfuran-3-yl)methanol

HRID 1877076

反応式

HRID 1877076 の反応式
[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[CH2:26][CH2:25][C:20]2([O:24][CH2:23][CH2:22][O:21]2)[CH2:19][CH2:18]1.O1CCCC1.Cl.O>O1CCCC1>[O:21]1[C:20]2([CH2:25][CH2:26][CH:17]([CH:7]([C:6]3[CH:5]=[C:4]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[O:3][C:2]=3[CH3:1])[OH:8])[CH2:18][CH2:19]2)[O:24][CH2:23][CH2:22]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 27953132-Methyl-5-phenyl-3-furaldehydeHCID 178420630HCID 178420630、化合物

生成物 1

HCID 685111101,4-Dioxaspiro[4.5]dec-8-yl(2-methyl-5-phenylfuran-3-yl)methanol収率 91%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-methyl-5-phenylfuran-3-carbaldehyde (2.4 g) in tetrahydrofuran (30 mL) was added dropwise 0.4N bromo(1,4-dioxaspiro[4.5]dec-8-yl)magnesium-tetrahydrofuran solution (33.5 mL) at 0° C. and, after the completion of the dropwise addition, the mixture was stirred at 0° C. for 1 hr. 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 (0% ethyl acetate/hexane to 30% ethyl acetate/hexane) to give the title compound (3.9 g, 91%) as a yellow crystal.

後処理

  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 (0% ethyl acetate/hexane to 30% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-ce0fe931b60c439dac559fca343f0011
出典データセット
uspto-grants-2012_11
特許番号
US08309580B2

関連ノート

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