2,2-Difluoropropane-1,3-diol → 1,3-Dioxane, 5,5-difluoro-2-[(phenylmethoxy)methyl]-

HRID 1645615

反応式

HRID 1645615 の反応式
[F:1][C:2]([F:7])([CH2:5][OH:6])[CH2:3][OH:4].[CH2:8]([O:15][CH2:16][CH:17]=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:8]([O:15][CH2:16][CH:17]1[O:6][CH2:5][C:2]([F:7])([F:1])[CH2:3][O:4]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 957442,2-Difluoropropane-1,3-diolHCID 108989(Phenylmethoxy)acetaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 597924871,3-Dioxane, 5,5-difluoro-2-[(phenylmethoxy)methyl]-収率 42.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2,2-difluoropropane-1,3-diol (1 g, 8.9 mmol), benzyloxyacetaldehyde (1.34 g, 8.9 mmol), p-toluenesulfonic acid monohydrate (154 mg, 0.81 mmol) and toluene (20 ml) was heated under reflux by a condenser equipped with a Dean-Stark apparatus for one hour. The resultant mixture was stirred at room temperature overnight and then the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and silica gel was added thereto. The resultant mixture was concentrated to dryness and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=10/1) to obtain the title compound (930 mg, 42.8%).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux by a condenser
  3. customequipped with a Dean-Stark apparatus for one hour
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. additionsilica gel was added
  7. concentrationThe resultant mixture was concentrated to dryness
  8. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-9b734eb25c01494e80c707d8bab73143
出典データセット
uspto-grants-2012_02
特許番号
US08124780B2

関連ノート

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