Tetrabutylammonium Fluoride → 4-Ethynyloxan-4-ol

HRID 2422489노트

반응식

HRID 2422489 반응식
C[Si]([C:5]#[C:6][C:7]1([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[C:6]([C:7]1([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)#[CH:5]

참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 597748684-[2-(Trimethylsilyl)ethynyl]oxan-4-ol

생성물 1

HCID 155504854-Ethynyloxan-4-ol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-{(trimethylsilyl)ethynyl}tetrahydropyran-4-ol (1.0 g, 5.04 mmol) in THF (SnL), a 1 M solution of tetrabutyl ammonium fluoride in THF (5.29 mL, 5.29 mmol) was added and the reaction was stirred 2 hours at room temperature. The reaction mixture was then poured into an aqueous 5% NH4OAc solution and diluted with ethyl acetate. The isolated organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was used as such for the next step. 1H NMR (400 MHz, acetone-d6): 4.61 (s, 1H), 3.87-3.77 (m, 2H), 3.60-3.50 (m, 2H), 2.98 (s, 1H), 1.89-1.81 (m, 2H), 1.77-1.65 (m, 2H).

후처리

  1. washThe isolated organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9d6ba52f372140779a9b635a6da2a1cb
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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