Iodoethane → Methyl acetate hexane

HRID 237861

반응식

HRID 237861 반응식
[H-].[Na+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][CH2:10][C:11]#[C:12][CH2:13][OH:14].I[CH2:16][CH3:17]>CN(C=O)C>[CH3:8][O:3][C:4]([CH3:5])=[O:9].[CH3:4][CH2:5][CH2:6][CH2:7][CH2:16][CH3:17].[CH2:16]([O:14][CH2:13][C:12]#[C:11][CH2:10][O:9][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][O:3]1)[CH3:17]

참가 물질

6

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 111233154-(Tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

생성물 2

HCID 23449302Methyl acetate hexane수율 1%HCID 685294632-(4-Ethoxy-but-2-ynyloxy)-tetrahydro-pyran

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

An oven dried 500 ml RBF was charged with NaH (60% in mineral oil) (1.41 g, 35.3 mmol) and suspended in DMF (100 mL). The mixture was cooled to 0° C. and 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol (prepared in accordance with the procedures of Tamaru et al., Bull. Chem. Soc. Jpn., 1995, 1689-1705) (6.0 g, 35.3 mmol) was added. The reaction mixture was allowed to reach room temperature and stirred for one hour. To the mixture was added iodoethane (20.8 g, 133 mmol). The reaction mixture was stirred for 3.5 hours at room temperature before being quenched with ice/H2O and extracted with MeOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (1-20% MeOAc/hexane) provided 4.71 g of 2-(4-ethoxy-but-2-ynyloxy)-tetrahydro-pyran as a clear oil.

후처리

  1. customAn oven dried 500 ml RBF
  2. addition, 1995, 1689-1705) (6.0 g, 35.3 mmol) was added
  3. customto reach room temperature
  4. stirringThe reaction mixture was stirred for 3.5 hours at room temperature
  5. custombefore being quenched with ice/H2O
  6. extractionextracted with MeOAc
  7. washThe organic phase was washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fd436759d4e74f2f98770a0ccab266a0
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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