Ammonium Chloride → 4-Ethynyloxan-4-ol

HRID 333886

反応式

HRID 333886 の反応式
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[C:8]([Mg]Cl)#[CH:9].[NH4+].[Cl-]>C1COCC1>[C:8]([C:4]1([OH:7])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)#[CH:9]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178462451HCID 178462451、化合物

生成物 1

HCID 155504854-Ethynyloxan-4-ol収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A stirred solution of dihydro-2H-pyran-4(3H)-one (500 mg, 5.0 mmol) in dry THF (20 mL) was cooled to −70° C. and 0.5 M ethynylmagnesium chloride in THF (20 mL, 10 mmol) was added in a slow stream. The cooling bath was allowed to expire and the mixture was stirred as it warmed to rt. After 6 h, satd aq NH4Cl (20 mL) was added and the mixture was concentrated on the rotary evaporator. The aqueous residue was extracted with EtOAc (2×50 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to leave crude 4-ethynyltetrahydro-2H-pyran-4-ol (491 mg, 78%) as a brown oil. 1H NMR (CDCl3) 1.80 (m, 2H), 1.92 (m, 2H), 2.57 (s, 1H), 3.68 (m, 2H), 3.90 (m, 2H).

後処理

  1. additionwas added
  2. concentrationthe mixture was concentrated on the rotary evaporator
  3. extractionThe aqueous residue was extracted with EtOAc (2×50 mL)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-cfb7f9444b054bac963ee380e46a2402
出典データセット
uspto-grants-2014_11
特許番号
US08883778B2

関連ノート

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