Ammonium Chloride → 4-Ethynyloxan-4-ol

HRID 333886

반응식

HRID 333886 반응식
[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]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178462451HCID 178462451, 화합물

생성물 1

HCID 155504854-Ethynyloxan-4-ol수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-cfb7f9444b054bac963ee380e46a2402
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883778B2

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