Trimethylsilylacetylene → 4-[2-(Trimethylsilyl)ethynyl]oxan-4-ol

HRID 2422488노트

반응식

HRID 2422488 반응식
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].C([Li])CCC.[O:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1>C1COCC1>[CH3:1][Si:2]([C:5]#[C:6][C:15]1([OH:18])[CH2:16][CH2:17][O:12][CH2:13][CH2:14]1)([CH3:4])[CH3:3]

참가 물질

5

반응물 3

HCID 66111TrimethylsilylacetyleneHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418339Butyllithium

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of trimethylsilylacetylene (5 mL, 35.4 mmol) in THF (100 mL) cooled at −78° C., a 1.6M n-butyllithium in hexanes (22.1 mL, 35.4 mmol) was added dropwise. The solution was stirred for 30 min before tetrahydro-4H-pyran-4-one (3.47 mL, 37.2 mmol) was added. The temperature was slowly raised to room temperature and the reaction was stirred overnight. The reaction was quenched with a saturated ammonium chloride solution and the aqueous layer was extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue obtained was used as such for the next step. 1H NMR (400 MHz, acetone-d6): 4.60 (s, 1H), 3.85-3.75 (m, 2H), 3.61-3.51 (m, 2H), 1.98-1.87 (m, 2H), 1.74-1.66 (m, 2H), 0.16 (s, 9H).

후처리

  1. additionwas added
  2. customThe reaction was quenched with a saturated ammonium chloride solution
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6742ab907ec7466491b7741ba8f7ddfe
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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